Spirocyclic aromatic hydrocarbons (SAHs) and their synthetic methodologies

Current Organic Chemistry

Volumn 14, Issue 18, 2010, Pages 2169-2195

  Xie, Ling Hai ^a   Liang, Jing ^a   Song, Juan ^a   Yin, Cheng Rong ^a   Huang, Wei ^a  

^a NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Cruciform system; Light emitting materials; O halobiaryls; Organic semiconductors; Spiro compounds; Spirobifluorene

Indexed keywords

AMORPHOUS MATERIALS; AROMATIZATION; GLASS TRANSITION; HYDROCARBONS;

AMORPHOUS ORGANICS; BUILDING BLOCKES; CRUCIFORM Π-SYSTEM; HETEROATOMS; HIGH-GLASS TRANSITION TEMPERATURES; LIGHT EMITTING MATERIALS; O-HALOBIARYL; SPIRO-COMPOUNDS; SPIROBIFLUORENE; SYNTHETIC METHODOLOGY;

LIGHT EMISSION;

EID: 78649978072     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210793351599     Document Type: Article

References (185)

1. Clarkson, R. G.; Gomberg, M. Spirans with four aromatic radicals on the spiro carbon atom1. J. Am. Chem. Soc. 1930, 52, 2881-2891.
2. Poriel, C.; Ferrand, Y.; le Maux, P.; Paul, C.; Rault-Berthelot, J.; Simonneaux, G. Poly(ruthenium carbonyl spirobifluorenylporphyrin): a new polymer used as a catalytic device for carbene transfer. Chem. Commun. 2003, 2308-2309;
3. Poriel, C.; Ferrand, Y.; Juillard, S.; Le Maux, P.; Simonneaux, G. Synthesis and stereochemical studies of di and tetra 9,9'-spirobifluorene porphyrins: new building blocks for catalytic material. Tetrahedron 2004, 60, 145-158;
4. Poriel, C.; Ferrand, Y.; Le Maux, P.; Paul-Roth, C.; Simonneaux, G.; Rault-Berthelot, J. Anodic oxidation and physicochemical properties of various porphyrin-fluorenes or -spirobifluorenes: Synthesis of new polymers for heterogeneous catalytic reactions. J. Electroanal. Chem. 2005, 583, 92-103;
5. Poriel, C.; Martail, A.; Simonneaux, G. Facial discrimination in mono arylporphyrins: Synthesis and stereochemical behaviour of bis(ligated) monospirobifluorenylporphyrin ruthenium complexes. Inorg. Chem. Commun. 2007, 10, 627-630.
6. Smith, D. K.; Zingg, A.; Diederich, F. Dendroclefts: Optically active dendritic receptors for the selective recognition and chiroptical sensing of monosaccharide guests. Helv. Chim. Acta 1999, 82, 1225-1241;
7. Das, G.; Hamilton, A. D. Carbohydrate recognition: Enantioselective spirobifluorene diphosphonate receptors. Tetrahedron Lett. 1997, 38, 3675-3678;
8. Hernandez, J. V.; Almaraz, M.; Raposo, C.; Martin, M.; Lithgow, A.; Crego, M.; Caballero, C.; Moran, J. R. Chiral recognition of tartaric acid derivatives with chromenone-benzoxazole receptors and a spirobifluorene spacer. Tetrahedron Lett. 1998, 39, 7401-7404;
9. Tejeda, A.; Oliva, A. I.; Simon, L.; Grande, M.; Caballero, M. C.; Moran, J. R. A macrocyclic receptor for the chiral recognition of hydroxycarboxylates. Tetrahedron Lett. 2000, 41, 4563-4566.
10. Fournier, J. H.; Maris, T.; Wuest, J. D. Molecular tectonics. Porous hydrogen-bonded networks built from derivatives of 9,9 '-spirobifluorene. J. Org. Chem. 2004, 69, 1762-1775;
11. Demers, E.; Maris, T.; Wuest, J. D. Molecular tectonics. Porous hydrogen-bonded networks built from derivatives of 2,2',7,7'-Tetraphenyl-9,9'-spirobi[9H-fluorene]. Cryst. Growth Des. 2005, 5, 1227-1235;
12. Wong, K. T.; Liao, Y. L.; Peng, Y. C.; Wang, C. C.; Lin, S. Y.; Yang, C. H.; Tseng, S. M.; Lee, G. H.; Peng, S. M. A novel right-angled ligand that forms polymeric metal-organic frameworks with nanometer-sized square cavities. Cryst. Growth Des. 2005, 5, 667-671;
13. Holy, P.; Havlik, M.; Tichy, M.; Zavada, J.; Cisarova, I. Synthesis and self-assembly of 9,9'-spirobifluorene-2,2',7,7'-tetracarboxylic acid and its tetraamide. Non-catenated formation of achiral grid layers with large chiral pores. Collect. Czech. Chem. Commun. 2006, 71, 139-154.
14. Weber, J.; Thomas, A. Toward stable interfaces in conjugated polymers: Microporous poly(p-phenylene) and poly(phenyleneethynylene) based on a spirobifluorene building block. J. Am. Chem. Soc. 2008, 130, 6334-6335;
15. Schmidt, J.; Werner, M.; Thomas, A. Conjugated Microporous Polymer Networks via Yamamoto Polymerization. Macromolecules 2009, 42, 4426-4429;
16. Thomas, S.; Pinnau, I.; Du, N. Y.; Guiver, M. D. Pure- and mixed-gas permeation properties of a microporous spirobisindane-based ladder polymer (PIM-1). J. Membr. Sci. 2009, 333, 125-131.
17. Wong, K. T.; Ku, S. Y.; Cheng, Y. M.; Lin, X. Y.; Hung, Y. Y.; Pu, S. C.; Chou, P. T.; Lee, G. H.; Peng, S. M. Synthesis, structures, and photoinduced electron transfer reaction in the 9,9 '-spirobifluorene-bridged bipolar systems. J. Org. Chem. 2006, 71, 456-465;
18. Chiang, C. L.; Tseng, S. M.; Chen, C. T.; Hsu, C. P.; Shu, C. F. Influence of molecular dipoles on the photoluminescence and electroluminescence of dipolar spirobifluorenes. Adv. Funct. Mater. 2008, 18, 248-257.
19. Aviram, A. Molecules for memory, logic, and amplification. J. Am. Chem. Soc. 1988, 110, 5687-5692.
20. Tour, J. M.; Wu, R.; Schumm, J. S. Approaches to orthogonally fused conducting polymers for molecular electronics. J. Am. Chem. Soc. 1990, 112, 5662-5663;
21. Tour, J. M.; Wu, R.; Schumm, J. S. Extended orthogonally fused conducting oligomers for molecular electronic devices. J. Am. Chem. Soc. 1991, 113, 7064-7066.
22. Salbeck, J.; Yu, N.; Bauer, J.; Weiss rtel, F.; Bestgen, H. Low molecular organic glasses for blue electroluminescence. Synth. Met. 1997, 91, 209-215.
23. Bach, U.; Lupo, D.; Comte, P.; Moser, J. E.; Weissortel, F.; Salbeck, J.; Spreitzer, H.; Gratzel, M. Solid-state dye-sensitized mesoporous TiO2 solar cells with high photon-to-electron conversion efficiencies. Nature 1998, 395, 583-585.
24. Yu, W. L.; Pei, J.; Huang, W.; Heeger, A. J. Spiro-functionalized polyfluorene derivatives as blue light-emitting materials. Adv. Mater. 2000, 12, 828-831.
25. Chuen, C. H.; Tao, Y. T.; Wu, F. I.; Shu, C. F. White organic light-emitting diodes based on 2,7-bis(2,2-diphenylvinyl)-9,9 '-spirobifluorene: Improvement in operational lifetime. Appl. Phys. Lett. 2004, 85, 4609-4611;
26. Steuber, F.; Staudigel, J.; Stossel, M.; Simmerer, J.;Winnacker, A.; Spreitzer, H.; Weissortel, F.; Salbeck, J. White light emission from organic LEDs utilizing spiro compounds with high-temperature stability. Adv. Mater. 2000, 12, 130-133.
27. Saragi, T. P. I.; Fuhrmann-Lieker, T.; Salbeck, J. High ON/OFF ratio and stability of amorphous organic field-effect transistors based on spiro-linked compounds. Synth. Met. 2005, 148, 267-270;
28. Nakanotani, H.; Akiyama, S.; Ohnishi, D.; Moriwake, M.; Yahiro, M.; Yoshihara, T.; Tobita, S.; Adachi, C. Extremely low-threshold amplified spontaneous emission of 9,9'-spirobifluorene derivatives and electroluminescence from field-effect transistor structure. Adv. Funct. Mater. 2007, 17, 2328-2335;
29. Saragi, T. P.; Fuhrmann-Lieker, T.; Salbeck, J. Comparison of charge-carrier transport in thin films of spiro-linked compounds and their corresponding parent compounds. Adv. Funct. Mater. 2006, 16, 966-974.
30. Xia, R.D.; Heliotis, G.; Campoy-Quiles, M.; Stavrinou, P. N.; Bradley, D. D. C.; Vak, D.; Kim, D. Y. Characterization of a high-thermal-stability spiroanthracenefluorene-based blue-light-emitting polymer optical gain medium. J. Appl. Phys. 2005, 98, 083101-7;
31. Spehr, T.; Siebert, A.; Fuhrmann-Lieker, T.; Salbeck, J.; Rabe, T.; Riedl, T.; Johannes, H. H.; Kowalsky, W.; Wang, J.; Weimann, T.; Hinze, P. Organic solid-state ultraviolet-laser based on spiro-terphenyl. Appl. Phys. Lett. 2005, 87, 3;
32. Schneider, D.; Rabe, T.; Riedl, T.; Dobbertin, T.; Werner, O.; Kroger, M.; Becker, E.; Johannes, H. H.; Kowalsky, W.; Weimann, T.; Wang, J.; Hinze, P.; Gerhard, A.; Stossel, P.; Vestweber, H. Deep blue widely tunable organic solid-state laser based on a spirobifluorene derivative. Appl. Phys. Lett. 2004, 84, 4693-4695;
33. Johansson, N.; Salbeck, J.; Bauer, J.; Weissortel, F.; Broms, P.; Andersson, A.; Salaneck, W. R. Solid-state amplified spontaneous emission in some spiro-type molecules: A new concept for the design of solid-state lasing molecules. Adv. Mater. 1998, 10, 1136-1141.
34. Rashidnadimi, S.; Hung, T. H.; Wong, K. T.; Bard, A. J. Electrochemistry and electrogenerated chemiluminescence of 3,6-Di(spirobifluorene)-N-phenylcarbazole. J. Am. Chem. Soc. 2008, 130, 634-639;
35. Sartin, M. M.; Shu, C. F.; Bard, A. J. Electrogenerated chemiluminescence of a spirobifluorene-linked bisanthracene: A possible simultaneous, two-electron transfer. J. Am. Chem. Soc. 2008, 130, 5354-5360;
36. Omer, K. M.; Ku, S. Y.; Wong, K. T.; Bard, A. J. Green Electrogenerated Chemiluminescence of Highly Fluorescent Benzothiadiazole and Fluorene Derivatives. J. Am. Chem. Soc. 2009, 131, 10733-10741;
37. Fungo, F.; Wong, K. T.; Ku, S. Y.; Hung, Y. Y.; Bard, A. J. Electrogenerated chemiluminescence. 81. Influence of donor and acceptor substituents on the ECL of a spirobifluorene-bridged bipolar system. J. Phys. Chem. B 2005, 109, 3984-3989;
38. Wakasugi, T.; Fujimori, K.; Matsumoto, M. Kinetics of base catalyzed chemiluminescence reaction of spiro[adamantane-1,3 '-(4 '-(m-hydroxyphenyl)-4'-methoxy-1',2 '-dioxetane)]. Chem. Lett. 2002, 762-763;
39. Mitschke, U.; Bauerle, P. Synthesis, characterization, and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes. J. Chem. Soc.-Perkin Trans. 1 2001, 740-753.
40. Ning, Z. J.; Zhang, Q.; Pei, H. C.; Luan, J. F.; Lu, C. G.; Cui, Y. P.; Tian, H. Photovoltage Improvement for Dye-Sensitized Solar Cells via Cone-Shaped Structural Design. J. Phys. Chem. C 2009, 113, 10307-10313.
41. Saragi, T. P. I.; Onken, K.; Suske, I.; Fuhrmann-Lieker, T.; Salbeck, J. Ambipolar organic phototransistor. Opt. Mater. 2007, 29, 1332-1337;
42. Saragi, T. P. I.; Pudzich, R.; Fuhrmann-Lieker, T.; Salbeck, J. Ultraviolet-sensitive field-effect transistor utilized amorphous thin films of organic donor/acceptor dyad. Appl. Phys. Lett. 2007, 90, 3;
43. Saragi, T. P. I.; Londenberg, J.; Salbeck, J. Photovoltaic and photoconductivity effect in thin-film phototransistors based on a heterocyclic spiro-type molecule. J. Appl. Phys. 2007, 102, 3;
44. Saragi, T. P. I.; Pudzich, R.; Fuhrmann, T.; Salbeck, J. Organic phototransistor based on intramolecular charge transfer in a bifunctional spiro compound. Appl. Phys. Lett. 2004, 84, 2334-2336.
45. Marsitzky, D.; Murray, J.; Scott, C.; Carter, K. R. Amorphous poly-2,7-fluorene networks. Chem. Mater 2001, 13, 4285-4289;
46. Geng, Y. H.; Katsis, D.; Culligan, S. W.; Ou, J. J.; Chen, S. H.; Rothberg, L. J. Fully spiro-configured terfluorenes as novel amorphous materials emitting blue light. Chem. Mater 2002, 14, 463-470;
47. Shen, W. J.; Dodda, R.; Wu, C. C.; Wu, F. I.; Liu, T. H.; Chen, H. H.; Chen, C. H.; Shu, C. F. Spirobifluorene-linked bisanthracene: An efficient blue emitter with pronounced thermal stability. Chem. Mater 2004, 16, 930-934.
48. Tang, S.; Liu, M.; Lu, P.; Xia, H.; Li, M.; Xie, Z. Q.; Shen, T. Z.; Gu, C.; Wang, H. P.; Yang, B.; Ma, Y. G. A molecular glass for deep-blue organic light-emitting diodes comprising a 9,9'-spirohifluorene core and peripheral carbazole groups. Adv. Funct. Mater. 2007, 17, 2869-2877.
49. Su, H. J.; Wu, F. I.; Shu, C. F. Tuning wavelength: Synthesis and characterization of spiro-DPVF-containing polyfluorenes and applications in organic light-emitting diodes. Macromolecules 2004, 37, 7197-7202.
50. Chiang, C.; Wu, M.; Dai, D.; Wen, Y.; Wang, J.; Chen, C. Red-emitting fluorenes as efficient emitting hosts for non-doped, organic red-light-emitting diodes. Adv. Funct. Mater. 2005, 15, 231-238.
51. Tsuzuki, T.; Tokito, S. Highly efficient and stable organic light-emitting diode using 4,4(')-bis(N-carbazolyl)-9,9(')-spirobifluorene as a thermally stable host material. Appl. Phys. Lett. 2009, 94, 3.
52. Yao, J. H.; Zhen, C. G.; Loh, K. P.; Chen, Z. K. Novel iridium complexes as high-efficiency yellow and red phosphorescent light emitters for organic light-emitting diodes. Tetrahedron 2008, 64, 10814-10820.
53. Xie, L.-H.; Zhu, R.; Qian, Y.; Liu, R.-R.; Chen, S.-F.; Lin, J.; Huang, W. Spiro-functionalized Ligand with Supramolecular Steric Hindrance to Control π-π Interaction in the Iridium Complex for High-Performance Electrophosphorescent Devices. J. Phys. Chem. Lett. 2010, 1, 272-276.
54. Saragi, T. P. I.; Spehr, T.; Siebert, A.; Fuhrmann-Lieker, T.; Salbeck, J. Spiro compounds for organic optoelectronics. Chem. Rev. 2007, 107, 1011-1065.
55. Fuhrmann, T.; Salbeck, J. Organic materials for photonic devices. MRS Bull. 2003, 28, 354-359.
56. Minkin, V. I. Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds. Chem. Rev. 2004, 104, 2751-2776.
57. Wu, R. L.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. Convergent synthetic routes to orthogonally fused conjugated oligomers directed toward molecular scale electronic device applications. J. Org. Chem. 1996, 61, 6906-6921.
58. Wu, Y. G.; Li, J.; Fu, Y. Q.; Bo, Z. S. Synthesis of extremely stable blue light emitting poly(spirobifluorene)s with suzuki polycondensation. Org. Lett. 2004, 6, 3485-3487.
59. Kim, K. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Blue light-emitting OLED using new spiro[fluorene-7,9 '-benzofluorene] host and dopant materials. Org. Electron. 2008, 9, 797-804.
60. Kim, K. S.; Jeon, Y. M.; Lee, H. S.; Kim, J. W.; Lee, C. W.; Jang, J. G.; Gong, M. S. Blue organic electroluminescent devices based on the spiro[fluorene-7,9 '-benzofluorene] derivatives as host and dopant materials. Synth. Met. 2008, 158, 870-875.
61. Jeon, S. O.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Spiro[fluorene-7,9 '-benzofluorene] host and dopant materials for blue light-emitting electroluminescence device. Synth. Met. 2009, 159, 1147-1152.
62. Jeon, S. O.; Lee, H. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Electroluminescent Properties of Spiro[fluorene-benzofluorene]-Containing Blue Light Emitting Materials. Bull. Korean Chem. Soc. 2009, 30, 863-868.
63. Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Blue organic light-emitting diodes using novel spiro[fluorene-benzofluorene]-type host materials. Dyes Pigment. 2009, 83, 66-71.
64. Kim, J. H.; Jeon, Y. M.; Jang, J. G.; Ryu, S.; Chang, H. J.; Lee, C. W.; Kim, J. W.; Gong, M. S. Blue OLEDs Utilizing Spiro[fluorene-7,9 '-benzofluorene]-type Compounds as Hosts and Dopants. Bull. Korean Chem. Soc. 2009, 30, 647-652.
65. Kim, K. S.; Lee, H. S.; Jeon, Y. M.; Kim, J. W.; Lee, C. W.; Gong, M. S. Blue light-emitting diodes from 2-(10-naphthylanthracene)-spiro[fluorene-7, 9 '-benzofluorene] host material. Dyes Pigm. 2009, 81, 174-179.
66. Liu, F.; Xie, L. H.; Tang, C.; Liang, J.; Chen, Q. Q.; Peng, B.; Wei, W.; Cao, Y.; Huang, W. Facile Synthesis of Spirocyclic Aromatic Hydrocarbon Derivatives Based on o-Halobiaryl Route and Domino Reaction for Deep-Blue Organic Semiconductors. Org. Lett. 2009, 11, 3850-3853.
67. Lee, H. Y.; Oh, J. Y.; Chu, H. Y.; Lee, J. I.; Kim, S. H.; Yang, Y. S.; Kim, G. H.; Do, L. M.; Zyung, T.; Lee, J.; Park, Y. Synthesis of regio- and stereoselective alkoxy-substituted spirobifluorene derivatives for blue light emitting materials. Tetrahedron 2003, 59, 2773-2779.
68. Lee, J. I.; Chu, H. Y.; Lee, H.; Oh, J.; Do, L. M.; Zyung, T.; Lee, J.; Shim, H. K. Solution-processible blue-light-emifting polymers based on alkoxy-substituted poly(spirobifluorene). ETRI J. 2005, 27, 181-187.
69. Shin, D. C.; Kim, Y. H.; You, H.; Kwon, S. K. Sterically hindered and highly thermal stable spirobifluorenyl-substituted poly(p-phenylenevinylene) for light-emitting diodes. Macromolecules 2003, 36, 3222-3227.
70. Kim, Y. H.; Kim, H. S.; Kwon, S. K. Synthesis and characterization of highly soluble and oxygen permeable new polyimides based on twisted biphenyl dianhydride and spirobifluorene diamine. Macromolecules 2005, 38, 7950-7956.
71. Yao, T. L.; Campo, M. A.; Larock, R. C. Synthesis of polycyclic aromatic iodides via ICI-induced intramolecular cyclization. Org. Lett. 2004, 6, 2677-2680.
72. Yao, T. L.; Campo, M. A.; Larock, R. C. Synthesis of polycyclic aromatics and heteroaromatics via electrophilic cyclization. J. Org. Chem. 2005, 70, 3511-3517.
73. Weisburger, J. H.; Weisburger, E. K.; Ray, F. E. The Structure of Fluorene. J. Am. Chem. Soc. 1950, 72, 4250-4253.
74. Jiang, Z. Q.; Yao, H. Q.; Zhang, Z. Q.; Yang, C. L.; Liu, Z. Y.; Tao, Y. T.; Qin, J. G.; Ma, D. G. Novel Oligo-9,9 '-spirobifluorenes through ortho-Linkage as Full Hydrocarbon Host for Highly Efficient Phosphorescent OLEDs. Org. Lett. 2009, 11, 2607-2610.
75. Weisburger, J.; Weisburger, E.; Ray, F. Some Derivatives of 9, 9'-Spirobifluorene. J. Am. Chem. Soc. 1950, 72, 4253-4255.
76. Pei, J.; Ni, J.; Zhou, X. H.; Cao, X. Y.; Lai, Y. H. Regioregular head-to-tail oligothiophene-functionalized 9,9 '-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties. J. Org. Chem. 2002, 67, 8104-8113.
77. Pei, J.; Ni, J.; Zhou, X. H.; Cao, X. Y.; Lai, Y. H. Head-to-tail regioregular oligothiophene-functionalized 9,9'-spirobifluorene derivatives. 1. Synthesis. J. Org. Chem. 2002, 67, 4924-4936.
78. Vak, D.; Chun, C.; Lee, C. L.; Kim, J. J.; Kim, D. Y. A novel spiro-functionalized polyfluorene derivative with solubilizing side chains. J. Mater. Chem. 2004, 14, 1342-1346.
79. Wei, Y.; Chen, C. T. Doubly ortho-linked cis-4,4'-bis(diarylamino)stilbene/fluorene hybrids as efficient nondoped, sky-blue fluorescent materials for optoelectronic applications. J. Am. Chem. Soc. 2007, 129, 7478-7479.
80. Song, S.; Jin, Y.; Kim, J.; Park, S. H.; Kim, S. H.; Lee, K.; Suh, H. A novel conjugated polymer based on cyclopenta[def]phenanthrene backbone with spiro group. Polymer 2008, 49, 5643-5649.
81. Campo, M. A.; Larock, R. C. Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls. Org. Lett. 2000, 2, 3675-3677.
82. Campo, M. A.; Larock, R. C. Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls. J. Org. Chem. 2002, 67, 5616-5620.
83. Zhai, L. Y.; Shukla, R.; Rathore, R. Oxidative C-C Bond Formation (Scholl Reaction) with DDQ as an Efficient and Easily Recyclable Oxidant. Org. Lett. 2009, 11, 3474-3477.
84. Thiemann, F.; Piehler, T.; Haase, D.; Saak, W.; Lutzen, A. Synthesis of enantiomerically pure dissymmetric 2,2 '-disubstituted 9,9 '-spirobifluorenes. Eur. J. Org. Chem. 2005, 1991-2001.
85. Cheng, X.; Hou, G. H.; Xie, J. H.; Zhou, Q. L. Synthesis and optical resolution of 9,9'-spirobifluorene-1, 1'-diol. Org. Lett. 2004, 6, 2381-2383.
86. Cheng, X.; Zhu, S. F.; Qiao, X. C.; Yan, P. C.; Zhou, Q. L. A general synthetic route to chiral dihydroxy-9,9 '-spirobifluorenes. Tetrahedron 2006, 62, 8077-8082.
87. Chiang, C. L.; Shu, C. F.; Chen, C. T. Improved synthesis of 2,2'-dibromo-9,9'-spirobifluorene and its 2,2'-bisdonor-7,7'-bisacceptorsubstituted fluorescent derivatives. Org. Lett. 2005, 7, 3717-3720.
88. Grisorio, R.; Suranna, G. P.; Mastrorilli, P.; Nobile, C. F. Insight into the role of oxidation in the thermally induced green band in fluorene-based systems. Adv. Funct. Mater. 2007, 17, 538-548.
89. Baker, W. The condesation of catechol with acetone. J. Chem. Soc. 1934, 1678-1681.
90. Frank, N. L.; Clerac, R.; Sutter, J. P.; Daro, N.; Kahn, O.; Coulon, C.; Green, M. T.; Golhen, S.; Ouahab, L. Synthesis, crystal structure, magnetic, and electron paramagnetic resonance properties of a spiroconjugated biradical. Evidence for spiroconjugation exchange pathway. J. Am. Chem. Soc. 2000, 122, 2053-2061.
91. Baker, W.; Williams, H. L. Some bis-1: 1' -spiroindanes. J. Chem. Soc. 1959, 1295-1299.
92. Carta, M.; Msayib, K. J.; Budd, P. M.; McKeown, N. B. Novel spirobisindanes for use as precursors to polymers of intrinsic microporosity. Org. Lett. 2008, 10, 2641-2643.
93. Wu, F. I.; Dodda, R.; Jakka, K.; Huang, J. H.; Hsu, C. S.; Shu, C. F. Enhancing the thermal and spectral stabilities of polyfluorene-based bluelight-emitting materials by incorporating pendent spiro-cycloalkyl groups. Polymer 2004, 45, 4257-4263.
94. Chen, C. H.; Shen, W. J.; Jakka, K.; Shu, C. F. Synthesis and characterization of spiro(adamantane-2,9 '-fluorene)-based triaryldiamines: thermally stable hole-transporting materials. Synth. Met. 2004, 143, 215-220.
95. Baldwin, S. The Synthesis of Spiro[cyclohexane-1,9'-fluorene] and Related Compounds1. J. Org. Chem. 1961, 26, 3280-3287.
96. Stauffer, D. A.; Fancher, O. E. Spiro[cyclohexane-1,9'-fluoren]-4-one and Some 4-Amino Derivatives. J. Org. Chem. 1960, 25, 935-938.
97. Zhang, X.; Bu, L.; Qu, Y.; Wang, L.; Geng, Y.; Wang, F. Novel spiro-fluorenes from tandem radical addition for liquid crystalline monodisperse conjugated oligomers. J. Mater. Chem. 2009, 19, 399-408.
98. Mechoulam, R.; Sondheimer, F. The Wittig Reaction with Fluorenone. Formation of Cyclopropane Derivatives. J. Am. Chem. Soc. 1958, 80, 4386-4388.
99. Greenwald, R.; Chaykovsky, M.; Corey, E. The Wittig Reaction Using Methylsulfinyl Carbanion-Dimethyl Sulfoxide 1. J. Org. Chem. 1963, 28, 1128-1129.
100. Greenwald, R.; Chaykovsky, M.; Corey, E. J. The Wittig Reaction Using Methylsulfinyl Carbanion-Dimethyl Sulfoxide 1. J. Org. Chem. 1963, 28, 1128-1129.
101. Jason, M.; Kurzweil, P.; Cahn, C. A Large-Scale Synthesis of Spiro [Cyclopropane-1, 9'-[9H] Fluorene] and Derivatives. Synth. Commun. 1981, 11, 865-873.
102. Alder, R. W.; Anderson, K. R.; Benjes, P. A.; Butts, C. P.; Koutentis, P.A.; Orpen, A. G. Polymers and oligomers with transverse aromatic groups and tightly controlled chain conformations. Chem. Commun. 1998, 309-310.
103. Wang, Z. X.; Shao, H. X.; Ye, J. C.; Zhang, L.; Lu, P. Substituent effects on crosslike packing of 2 ',7 '-diaryl-spiro(cyclopropane-1,9 '-fluorene) derivatives: Synthesis and crystallographic, optical, and thermal properties. Adv. Funct. Mater. 2007, 17, 253-263.
104. Matsumoto, M.; Takamido, Y.; Nomura, K.; Shiono, T.; Watanabe, N.; Ijuin, H. K. Marked difference in singlet-chemiexcitation efficiency between syn-anti isomers of spiro[1,2-dioxetane-3,1'-dihydroisobenzofuran] for intramolecular charge-transfer-induced decomposition. Tetrahedron Lett. 2008, 49, 6145-6147.
105. Destri, S.; Pasini, M.; Botta, C.; Porzio, W.; Bertini, F.; Marchio, L. Synthesis and crystal structure and optical properties of fluorenic-core oligomers. J. Mater. Chem. 2002, 12, 924-933.
106. Tseng, Y. H.; Shih, P. I.; Chien, C. H.; Dixit, A. K.; Shu, C. F.; Liu, Y. H.; Lee, G. H. Stable organic blue-light-emitting devices prepared from poly[spiro(fluorene-9,9'-xanthene)]. Macromolecules 2005, 38, 10055-10060;
107. Xie, L. H.; Liu, F.; Tang, C.; Hou, X. Y.; Hua, Y. R.; Fan, Q. L.; Huang, W. Unexpected one-pot method to synthesize spiro[fluorene-9,9 '-xanthene] building blocks for blue-light-emitting materials. Org. Lett. 2006, 8, 2787-2790.
108. Baum, G.; Bernard, R.; Shechter, H. Diradical processes in decomposition of spiro-[fluorene-9, 3'-indazole]. J. Am. Chem. Soc. 1967, 89, 5307-5308.
109. Baum, G.; Shechter, H. Carbenic processes in decomposition of spiro [fluorene-9, 3'-indazole]. Simple route to the fluoradene system. J. Org. Chem. 1976, 41, 2120-2124.
110. Wong, K. T.; Chen, R. T.; Fang, F. C.; Wu, C. C.; Lin, Y. T. 4,5-diazafluorene-incorporated ter(9,9-diarylfluorene): A novel molecular doping strategy for improving the electron injection property of a highly efficient OLED blue emitter. Org. Lett. 2005, 7, 1979-1982.
111. Chen, C. T.; Wei, Y.; Lin, J. S.; Moturu, M.; Chao, W. S.; Tao, Y. T.; Chien, C. H. Doubly ortho-linked quinoxaline/diphenylfluorene hybrids as bipolar, fluorescent chameleons for optoelectronic applications. J. Am. Chem. Soc. 2006, 128, 10992-10993.
112. Vak, D.; Shin, S. J.; Yum, J. H.; Kim, S. S.; Kim, D. Y. Blue electroluminescence from spiro-configured polyfluorene derivatives with hetero-atoms. J. Lumines. 2005, 115, 109-116.
113. Vak, D.; Jo, J.; Ghim, J.; Chun, C.; Lim, B.; Heeger, A. J.; Kim, D. Y. Synthesis and characterization of spiro-triphenylamine configured polyfluorene derivatives with improved hole injection. Macromolecules 2006, 39, 6433-6439.
114. Katsis, D.; Geng, Y. H.; Ou, J. J.; Culligan, S. W.; Trajkovska, A.; Chen, S. H.; Rothberg, L. J. Spiro-linked ter-, penta-, and heptafluorenes as novel amorphous materials for blue light emission. Chem. Mat. 2002, 14, 1332-1339.
115. Huang, B.; Jiang, Z. Q.; Li, J.; Qin, J. G.; Yu, G.; Liu, Y. Q. A new polyquinoline containing spirobifluorene and phenathiazine units with excellent electroluminescence properties. Chem. Lett. 2005, 34, 1048-1049.
116. Huang, B.; Li, J.; Jiang, Z. Q.; Qin, J. G.; Yu, G.; Liu, Y. Q. New series of light-emitting polyquinolines containing 9,9'-spirobifluorene units. Macromolecules 2005, 38, 6915-6922.
117. Chen, C. H.; Wu, F. I.; Shu, C. F.; Chien, C. H.; Tao, Y. T. Spirobifluorene-based pyrazoloquinolines: efficient blue electroluminescent materials. J. Mater. Chem. 2004, 14, 1585-1589.
118. Wynberg, H.; Heeres, G. J.; Jordens, P.; Sinnige, H. J. M. Synthesis and spectra of some heterocyclic conjugated spiranes. Recl. Trav. Chim. Pays-Bas 1970, 89, 544.
119. Ong, T. T.; Ng, S. C.; Chan, H. S. O.; Vardhanan, R. V.; Kumura, K.; Mazaki, Y.; Kobayashi, K. Development of a novel isotype organic heterojunction diode consisting of poly{7-spiro(9-fluorenyl)cyclopentadithiophene} and poly(3-octylthiophene). J. Mater. Chem. 2003, 13, 2185-2188.
120. Xie, L. H.; Hou, X. Y.; Hua, Y. R.; Tang, C.; Liu, F.; Fan, Q. L.; Huang, W. Facile synthesis of complicated 9,9-diarylfluorenes based on BF3 center dot Et2O-mediated Friedel-Crafts reaction. Org. Lett. 2006, 8, 3701-3704.
121. Xie, L. H.; Fu, T.; Hou, X. Y.; Tang, C.; Hua, Y. R.; Wang, R. J.; Fan, Q. L.; Peng, B.; Wei, W.; Huang, W. An efficient synthesis of novel spiro[[8H]indeno[2,1-b]-thiophene-8,9'-fluorene] building block for blue light-emitting materials. Tetrahedron Lett. 2006, 47, 6421-6424.
122. Kowada, T.; Matsuyama, Y.; Ohe, K. Synthesis, characterization, and photoluminescence of thiophene-containing spiro compounds. Synlett 2008, 1902-1906.
123. Xie, L. H.; Hou, X. Y.; Hua, Y. R.; Huang, Y. Q.; Zhao, B. M.; Liu, F.; Peng, B.; Wei, W.; Huang, W. An effective strategy to tune supramolecular interaction via a spiro-bridged spacer in oligothiophene-S,S-dioxides and their anomalous photoluminescent behavior. Org. Lett. 2007, 9, 1619-1622.
124. Londenberg, J.; Saragi, T. R. L.; Suske, I.; Salbeck, J. 4,4 '-spirobi[cyclopenta[ 2,1-b;3,4-b']dithiophene]: A new generation of heterocyclic spiro-type molecule. Adv. Mater. 2007, 19, 4049-4053.
125. Hatano, Y. The Chemistry of Fluoran Leuco Dyes. Chem. Appl. Leuco Dyes 1997, 159.
126. Sun, W.; Gee, K.; Klaubert, D.; Haugland, R. Synthesis of fluorinated fluoresceins. J. Org. Chem. 1997, 62, 6469-6475.
127. Wu, S. L.; Zhang, W. C.; Zhang, Z. G.; Zhang, X. M. Synthesis of new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzed asymmetric hydrogenation reactions. Org. Lett. 2004, 6, 3565-3567.
128. Bischoff, F.; Adkins, H. The condensation of diphenic anhydride with resorcinol. J. Am. Chem. Soc. 1923, 45, 1030-1033.
129. Sen, R. N.; Chattopadhya, N. C.; Sen-Gupta, S. C. J. Indian Chem. Soc. 1930, 7, 997.
130. Pankratov, V.; Korshak, V.; Vinogradova, S. Synthesis of polyarylates of 2, 7-dihydroxyxanthene-9, 9-spirofluorene. Russ. Chem. Bull. 1965, 14, 1256-1257.
131. McFarlane, S. L.; Coumont, L. S.; Piercey, D. G.; McDonald, R.; Veinot, J. G. C. One-Pot Synthesis of a Thermally Stable Blue Emitter: Poly[spiro(fluorene-9,9 '-(2 '-phenoxyxanthene)]. Macromolecules 2008, 41, 7780-7782.
132. Gilman, H.; Gorsich, R. D. Cyclic Organosilicon Compounds. I. Synthesis of Compounds Containing the Dibenzosilole Nucleus. J. Am. Chem. Soc. 1958, 80, 1883-1886.
133. Katkevics, M.; Yamaguchi, S.; Toshimitsu, A.; Tamao, K. From tellurophenes to siloles. Synthesis, structures, and photophysical properties of 3,4-unsubstituted 2,5-diarylsiloles. Organometallics 1998, 17, 5796-5800.
134. Russell, A. G.; Spencer, N. S.; Philp, D.; Kariuki, B. M.; Snaith, J. S. The first spirobifluorenes containing two binaphthyl moieties. Organometallics 2003, 22, 5589-5592.
135. Palilis, L. C.; Murata, H.; Uchida, M.; Kafafi, Z. H. High efficiency molecular organic light-emitting diodes based on silole derivatives and their exciplexes. Org. Electron. 2003, 4, 113-121.
136. Lee, S. H.; Jang, B. B.; Kafafi, Z. H. Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives. J. Am. Chem. Soc. 2005, 127, 9071-9078.
137. Ito, A.; Urabe, M.; Tanaka, K. A spiro-fused triarylaminium radical cation with a triplet ground state. Angew. Chem.-Int. Edit. 2003, 42, 921-924.
138. Couzijn, E. P. A.; Schakel, M.; de Kanter, F. J. J.; Ehlers, A. W.; Lutz, M.; Spek, A. L.; Lammertsma, K. Dynamic configurational isomerism of a stable pentaorganosilicate. Angew. Chem.-Int. Edit. 2004, 43, 3440-3442.
139. Couzijn, E. P. A.; van den Engel, D. W. F.; Slootweg, J. C.; de Kanter, F. J. J.; Ehlers, A. W.; Schakel, M.; Lammertsma, K. Configurationally Rigid Pentaorganosilicates. J. Am. Chem. Soc. 2009, 131, 3741-3751.
140. Ohshita, J.; Lee, K.; Hamamoto, D.; Kunugi, Y.; Ikadai, J.; Kwak, Y.; Kunai, A. Synthesis of novel spiro-condensed dithienosiloles and the application to organic FET. Chem. Lett. 2004, 33, 892-893.
141. Son, H. J.; Han, W. S.; Chun, J. Y.; Kwon, S. N.; Ko, J.; Kang, S. O. Enhanced charge-carrier mobility derived from Cyclization of a silanylene unit on dithienosiloles: syntheses, photophysical properties, and device fabrication of dithieno-spiro-siloles. Organometallics 2008, 27, 2464-2473.
142. Lee, H.; Kim, J.; Kang, Y. Structure and optical properties of new spirobisilole: 2,3,3',4,4',5-hexaphenyl-1,1'-siprobisilole. Inorg. Chem. Commun. 2007, 10, 731-734.
143. Lee, J.; Yuan, Y. Y.; Kang, Y. J.; Lia, W. L.; Lu, Z. H.; Wang, S. I. 2,5-Functionalized spiro-bisiloles as highly efficient yellow-light emitters in electroluminescent devices. Adv. Funct. Mater. 2006, 16, 681-686.
144. Matsuda, T.; Kadowaki, S.; Goya, T.; Murakami, M. Synthesis of Silafluorenes by Iridium-Catalyzed [2+ 2+ 2] Cycloaddition of Silicon-Bridged Diynes with Alkynes. Org. Lett. 2007, 9, 133-136.
145. Brown, D.; Massey, A.; Mistry, T. The crystal and molecular structure of 5, 5-diphenyloctafluorogermanthrene, (C6H5)2GeC12F8. J. Organomet. Chem. 1986, 302, 343-350.
146. Gelius, R. Dibenzostannole und ihre Abbauptodukte. Chem. Berichte 1960, 93, 1759-1768.
147. Georg, W.; Ernst, K. Zur Synthese von pentaarylierten Phosphoranen. Chem. Berichte 1964, 97, 741-746.
148. Hellwinkel, D.; Bach, M. Pentaorganyle des antimons. J. Organomet. Chem. 1969, 17, 389-403.
149. Dieter, H.; Gerhard, F. Bis-biphenylen-tellur. Tetrahedron Lett. 1965, 6, 1823-1827.
150. Van beelen, D. C.; Wolters, J.; Van der Gen, A. Recl. Trav. Chim. Pays-Bas 1979, 98, 437-440.
151. Xie, L. H.; Hou, X. Y.; Tang, C.; Hua, Y. R.; Wang, R. J.; Chen, R. F.; Fan, Q. L.; Wang, L. H.; Wei, W.; Peng, B.; Huang, W. Novel H-shaped persistent architecture based on a dispirlo building block system. Org. Lett. 2006, 8, 1363-1366.
152. Poriel, C.; Rault-Berthelot, J.; Barriere, F.; Slawin, A. M. Z. New dispiro compounds: Synthesis and properties. Org. Lett. 2008, 10, 373-376.
153. Thirion, D.; Poriel, C.; Barriere, F. d. r.; Metivier, R. m.; Jeannin, O.; Rault-Berthelot, J. l. Tuning the Optical Properties of Aryl-Substituted Dispirofluorene-Indenofluorene Isomers through Intramolecular Excimer Formation. Org. Lett. 2009, 11, 4794-4797.
154. Luo, J.; Lei, T.; Wang, L.; Ma, Y. G.; Cao, Y.; Wang, J.; Pei, J. Highly Fluorescent Rigid Supramolecular Polymeric Nanowires Constructed Through Multiple Hydrogen Bonds. J. Am. Chem. Soc. 2009, 131, 2076-2077.
155. Suzuki, T.; Ohta, E.; Kawai, H.; Fujiwara, K.; Fukushima, T. Dynamic redox systems as electrochromic materials: Bistability and advanced response. Synlett 2007, 851-869.
156. Suzuki, T.; Yamamoto, R.; Higuchi, H.; Hirota, E.; Ohkita, M.; Tsuji, T. Electrochiroptical response of a hexaarylethane derivative with a helical pi-skeleton: drastic UV-Vis and CD spectral changes upon electrolysis of 4 ',5 '-dibromodispiro xanthene-9,9 '(9 ' H, 10 ' H)-phenanthrene-10 ',9 ''-xanthene. J. Chem. Soc.-Perkin Trans. 2 2002, 1937-1942;
157. Suzuki, T.; Takeda, T.; Kawai, H.; Fujiwara, K. Ultralong C-C bonds in hexaphenylethane derivatives. Pure Appl. Chem. 2008, 80, 547-553.
158. Horhant, D.; Liang, J. J.; Virboul, M.; Poriel, C.; Alcaraz, G.; Rault-Berthelot, J. Dispirofluorene-indenofluorene (DSFIF): Synthesis, electrochemical, and optical properties of a promising new family of luminescent materials. Org. Lett. 2006, 8, 257-260.
159. Vak, D.; Lim, B.; Lee, S. H.; Kim, D. Y. Synthesis of a double spiro-polyindenofluorene with a stable blue emission. Org. Lett. 2005, 7, 4229-4232.
160. Wang, C. H.; Hu, R. R.; Liang, S.; Chen, J. H.; Yang, Z.; Pei, J. Linear C-2-symmetric polycyclic benzodithiophene: efficient, highly diversified approaches and the optical properties. Tetrahedron Lett. 2005, 46, 8153-8157.
161. Poriel, C.; Liang, J. J.; Rault-Berthelot, J.; Barriere, F.; Cocherel, N.; Slawin, A. M. Z.; Horhant, D.; Virboul, M.; Alcaraz, G.; Audebrand, N.; Vignau, L.; Huby, N.; Wantz, G.; Hirsch, L. Dispirofluorene-indenofluorene derivatives as new building blocks for blue organic electroluminescent devices and electroactive polymers. Chem. Eur. J. 2007, 13, 10055-10069.
162. Kimura, M.; Kuwano, S.; Sawaki, Y.; Fujikawa, H.; Noda, K.; Taga, Y.; Takagi, K. New 9-fluorene-type trispirocyclic compounds for thermally stable hole transport materials in OLEDs. J. Mater. Chem. 2005, 15, 2393-2398.
163. Luo, J.; Zhou, Y.; Niu, Z. Q.; Zhou, Q. F.; Ma, Y. G.; Pei, J. Three-dimensional architectures for highly stable pure blue emission. J. Am. Chem. Soc. 2007, 129, 11314.
164. Shi, Y. B.; Qian, H. L.; Lucas, N. T.; Xu, W.; Wang, Z. H. Synthesis of a three-dimensional spiro-annulated polycyclic aromatic hydrocarbon. Tetrahedron Lett. 2009, 50, 4110-4113.
165. Nishida, J.; Miyagawa, T.; Yamashita, Y. Novel thiophene oligomers containing a redox active hexaarylethane unit. Org. Lett. 2004, 6, 2523-2526.
166. Suzuki, T.; Ono, K.; Nishida, J.; Takahashi, H.; Tsuji, T. Preparation and molecular structures of 9,10-dihydrophenanthrenes: Substituent effects on the long bond length. J. Org. Chem. 2000, 65, 4944-4948.
167. Kawai, H.; Takeda, T.; Fujiwara, K.; Suzuki, T. Short nonbond and long C-C bond in naphthalene-1,8-diylbis(10-methylacridinium) and the corresponding hexaphenylethane derivative: a new electrochromic pair exhibiting dynamic redox properties. Tetrahedron Lett. 2004, 45, 8289-8293.
168. Suzuki, T.; Tanaka, S.; Higuchi, H.; Kawai, H.; Fujiwara, K. Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon: preparation, X-ray structures, and electrochromic response with fluorescence change. Tetrahedron Lett. 2004, 45, 8563-8567.
169. Kawai, H.; Takeda, T.; Fujiwara, K.; Inabe, T.; Suzuki, T. Exceptionally large difference in bond length among conformational isomorphs of a hexaphenylethane derivative with a dispiropyracene skeleton. Cryst. Growth Des. 2005, 5, 2256-2260.
170. Suzuki, T.; Tanaka, S.; Kawai, H.; Fujiwara, K. Multi-input-multi-output molecular response system based on dynamic redox behavior of hexaphenylethane-type electron donors with the tetrahydrophenanthrazepine skeleton: Strong chiroptical signals through the transmission of point chirality to helicity. Chem. Asian J. 2007, 2, 171-177.
171. Kawai, H.; Takeda, T.; Fujiwara, K.; Wakeshima, M.; Hinatsu, Y.; Suzuki, T. Ultralong carbon-carbon bonds in dispirobis(10-methylacridan) derivatives with an acenaphthene, pyracene, or dihydropyracylene skeleton. Chem. Eur. J. 2008, 14, 5780-5793.
172. Kurata, H.; Kim, S.; Fujimoto, T.; Matsumoto, K.; Kawase, T.; Kubo, T. Synthesis and functionalization of 3,3 '-bis(spirodienone)-Bridged 2,2 '-bithiophene: A new building block for redox-active molecular switching materials. Org. Lett. 2008, 10, 3837-3840.
173. Kurata, H.; Kim, S.; Matsumoto, K.; Kawase, T.; Oda, M. Photochemical and redox switching in a ring-closed isomer of thioindigo-extended quinone. Chem. Lett. 2007, 36, 386-387.
174. Wu, Y. G.; Zhang, J. Y.; Bo, Z. S. Synthesis of monodisperse spiro-bridged ladder-type oligo-p-phenylenes. Org. Lett. 2007, 9, 4435-4438.
175. Wu, Y. G.; Zhang, J. Y.; Fei, Z. P.; Bo, Z. S. Spiro-bridged ladder-type poly(p-phenylene)s: Towards structurally perfect light-emitting materials. J. Am. Chem. Soc. 2008, 130, 7192-7193.
176. Wang, B. L.; Forster, M.; Preis, E.; Wang, H.; Ma, Y. G.; Scherf, U. Simplified Synthesis of Spiro-Bridged Ladder-Type Poly(p-phenylene). J. Polym. Sci. Pol. Chem. 2009, 47, 5137-5143.
177. Yu, S. Q.; Lin, H. Y.; Zhao, Z. J.; Wang, Z. X.; Lu, P. Excellent blue fluorescent trispirobifluorenes: synthesis, optical properties and thermal behaviors. Tetrahedron Lett. 2007, 48, 9112-9115.
178. Li, L. C.; Xiang, J. F.; Xu, C. H. Synthesis of novel ladder bis-silicon-bridged p-terphenyls. Org. Lett. 2007, 9, 4877-4879.
179. Combes, C.; Cristau, H.; Li, W.; McPartlin, M.; Plenat, F.; Scowen, I. A novel C-bonded trispiro cyclotriphosphazene: synthesis and X-ray structural studies. Journal of chemical research. Synopses(Print) 1994, 134-135.
180. Combes-Chamalet, C.; Cristau, H.; McPartlin, M.; Plnat, F.; Scowen, I.; Woodroffe, T. Synthesis and X-ray structural studies of new spiro-cyclotriphosphazenes. J. Chem. Soc. Perkin Trans. 2 1997, 1997, 15-18.
181. Harrington, L. E.; Britten, J. F.; McGlinchey, M. J. Dimerization of 9-phenylethynylfluorene to Di- ndeno-naphthacene and dispiro-[fluorenedihydronaphthacenefluorene]: An X-ray crystallographic and NMR study. Org. Lett. 2004, 6, 787-790.
182. Banide, E. V.; Molloy, B. C.; Ortin, Y.; Muller-Bunz, H.; McGlinchey, M.J. From allenes to tetracenes: A synthetic and structural study of silyl- and halo-allenes and their dimers. Eur. J. Org. Chem. 2007, 2611-2622.
183. Banide, E. V.; Grealis, J. P.; Mueller-Bunz, H.; Ortin, Y.; Casey, M.; Mendicute-Fierro, C.; Lagunas, M. C.; McGlinchey, M. J. Chromium, iron, ruthenium and gold complexes of 3,3-(biphenyl-2,2 '-diyl)-1-diphenylphosphino-1-phenylallene: A versatile ligand. J. Organomet. Chem. 2008, 693, 1759-1770.
184. Banide, E. V.; Oulie, P.; McGlinchey, M. J. From allenes to tetracenes: Syntheses, structures, and reactivity of the intermediates. Pure Appl. Chem. 2009, 81, 1-17.
185. Banide, E. V.; Oulie, P.; Muller-Bunz, H.; McGlinchey, M. J. Unexpected Dimerization of a Bis(fluorenyl)-bis(trimethylsilyl)-diallene to a Dihydroquatercyclopentadiene, an Octacyclic C-36 Fragment Corresponding to 60% of C-60: Reaction of the Diallene with Fe-2(CO)(9). Organometallics 2008, 27, 5657-5664.