Selenophenes as Hetero-Analogues of Thiophene-Based Materials

Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics

Volumn , Issue , 2009, Pages 321-340

  Otsubo, Tetsuo ^a   Takimiya, Kazuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Amphoteric quinoidal selenophenes; Crystal structures of quaterselenophene; Electron donating selenophene fused tetrathiafulvalenes; Organic field effect transistors (OFETs); Selenophene materials as conductive, electroactive and OFET materials; Selenophene based electroactive materials; Selenophene based OFET materials; Selenophenes as hetero analogues of thiophene based materials

Indexed keywords

EID: 80054734200     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470745533.ch6     Document Type: Chapter

References (130)

1. J. Roncali, Conjugated poly(thiophenes): synthesis, functionalization and applications, Chem. Rev., 92, 711-738 (1992).
2. K. Kaeriyama, Synthesis and properties of processable polythiophenes, in Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 2, Chapter 8, pp. 271-308.
3. S. Hotta, Molecular conductive materials: polythiophenes and oligothiophenes, in Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 2, Chapter 8, pp. 309-387.
4. G. Schopf and G. Kossmehl, Polythiophenes-Electrically Conductive Polymers, Springer, Berlin, 1997.
5. R. D. McCullough, The chemistry of conducting polythiophenes, Adv. Mater., 10, 93-116 (1998).
6. P. Bauerle, Sulfur-containing oligomers, in Electronic Materials: the Oligomeric Approach, ed/K. Müllen and G. Wegner, Wiley-VCH Verlag GmbH, Weinheim, 1998, Chapter 2, pp. 105-197.
7. D. Fichou, Handbook of Oligo-and Polythiophenes, Wiley-VCH Verlag GmbH, Weinheim, 1999.
8. T. Otsubo, Y. Aso and K. Takimiya, Synthesis, optical and conductive properties of long oligothiophenes and their utilization as molecular wires, Bull. Chem. Soc. Jpn., 74, 1789-1801 (2001).
9. T. Otsubo, Y. Aso and K. Takimiya, Functional oligothiophenes as advanced molecular electronic materials, J. Mater. Chem., 12, 2565-2575 (2002).
10. T. Otsubo, Y. Aso and K. Takimiya, Fullerene-tethered oligothiophenes as advanced molecular electronics materials, Pure Appl. Chem., 77, 2003-2010 (2005).
11. N. M. Magdesieva and N. S. Zefirov, Selenophenes and related compounds, in Organic Selenium Compounds; Their Chemistry and Biology, ed. D. L. Klayman and W. H. H. Gunther, John Wiley & Sons, Inc., New York, 1973, pp. 427-457.
12. C. W. Bird, Selenophenes, in Comprehensive Heterocyclic Chemistry II, ed. L. E. E. Christiaens, Elsevier, Oxford, 1996, Vol. 2, pp. 730-748.
13. S. Gronowitz, Selenophene, a twin-brother of thiophene? Phosphorus Sulfur Silicon Relat. Elem., 136-138, 59-90 (1998).
14. A. Z. Djumanazarova, V. P. Litvinov and A. Konar, Charge-transfer complexes of some 5-membered condensed heteroaromatic systems with tetracyanoethylene, Chem. Scr., 20, 214-218 (1982).
15. K. Kamada, M. Ueda, T. Sakaguchi, K. Ohta and T. Fukumi, Femtosecond optical Kerr study of heavy atom effects on the third-order optical nonlinearity of thiophene homologues: purely electronic contribution, Chem. Phys. Lett., 263, 215-222 (1996).
16. G. L. Sommen, Synthesis of selenophenes, Mini-Rev. Org. Chem., 2, 375-388 (2005).
17. S. Mohmand, J. Bargon and R. J. Waltman, Improved synthesis of selenophene, J. Org. Chem., 48, 3544-3545 (1983).
18. J. Nakayama, R. Yomoda and M. Hoshino, Reactions of elemental sulfur and selenium with some acetylenic compounds. Formation of thiophenes and selenophenes, Heterocycles, 26, 2215-2222 (1987).
19. J. Nakayama, M. Kashiwagi, R. Yomoda and M. Hoshino, Reactions of elemental sulfur and selenium with dimethyl acetylenedicarboxylate, methyl propiolate and benzyne, Nippon Kagaku Kaishi, 1424-1429 (1987).
20. E. N. Deryagina and M. G. Voronkov, Thermal methods for the synthesis of thiophene, selenophene and their derivatives, Chem. Heterocycl. Compd., 36, 1-14 (2000).
21. W. Mack, Preparation of tetrachlorotellurophene and tetrachloroselenophene, Angew. Chem., 77, 260 (1965).
22. G. Barbey, G. Dian, N. Merlet, F. Outurquin and C. Paulmier, Direct synthesis of 3-methylselenophene and 3,4-dimethylselenophene, Synthesis, 181-182 (1989).
23. S. Tsuboi, S. Mimura, S. Ono, K. Watanabe and A. Takeda, Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furans and selenophenes, Bull. Chem. Soc. Jpn., 60, 1807-1812 (1987).
24. 2 with 1,3-dienes: selenophene formation, J. Org. Chem., 67, 6553-6556 (2002).
25. R. F. Curtis, S. N. Hasnain and J. A. Taylor, Selenophenes from diacetylenes, Chem. Commun., 365 (1968).
26. P. M. Jacobs, M. A. Davis and H. Norton, A semi-micro synthesis of selenophene, J. Heterocycl. Chem., 14, 115-116 (1977).
27. A. Ulman, J. Manassen, F. Frolow and D. Rabinovich, Synthesis of new tetraphenylporphyrin molecules containing heteroatoms other than nitrogen: II. Tetraphenyl-21-selena-23-thiaporphyrin and tetraphenyl-21,23-diselenaporphyrin, Tetrahedron Lett., 167-170 (1978).
28. J. Nakayama, M. Shibuya and M. Hoshino, Preparation of 2,5-diacylselenophenes by condensation of α,α'-diketo selenides with glyoxal, Heterocycles, 26, 909-912 (1987).
29. J. Nakayama, F. Murai, M. Hoshino and A. Ishii, A novel synthesis of selenophenes, Tetrahedron Lett., 29, 1399-1400 (1988).
30. P. J. Fagan and W. A. Nugent, Synthesis of main group heterocycles by metallacycle transfer from zirconium, J. Am. Chem. Soc., 110, 2310-2312 (1988).
31. P. Arsenyan, O. Pudova and E. Lukevics, A novel method for the synthesis of 2,5-diarylselenophenes, Tetrahedron Lett., 43, 4817-4819 (2002).
32. J. Morel, C. Paulmier, M. Garreau and G. Martin, Etude de selenophenes mono-et bisubstitutes. Determination d'increments structuraux additifs en resonance magnetique nucleaire, Bull. Soc. Chim. Fr., 12, 4497-4503 (1971).
33. X, J. Chem. Soc., Chem. Commun., 578-580 (1977).
34. M. D. Bezoari, P. Kovacic, S. Gronowitz and A. B. Hornfedt, Polymerization of aromatic nuclei. XXVIII. Synthesis and properties of poly(2,5-selenienylene), J. Polym. Sci., Polym. Lett. Ed., 19, 347-353 (1981).
35. J. P. Montheard, T. Pascal, G. Seytre, G. Steffan-Boiteux and A. Douillard, New semiconducting polymers from aromatic and heterocyclic nuclei and their doping with iodine, Synth. Met., 9, 389-396 (1984).
36. R. Sugimoto, K. Yoshino, S. Inoue and K. Tsukagoshi, Preparation and properties of polytellurophene and polyselenophene, Jpn. J. Appl. Phys., 24, L425-L427 (1985).
37. K. Yoshino, K. Kaneto, S. Inoue and K. Tsukagoshi, Electrochemical preparation of polyselenophene and its properties, Jpn. J. Appl. Phys., 22, L698-L699 (1983).
38. K. Yoshino, Y. Kohno, T. Shiraishi, K. Kaneto, S. Inoue and K. Tsukagoshi, Electrical and optical properties of electrochemically prepared polyselenophene film, Synth. Met., 10, 319-326 (1985).
39. S. Glenis, D. S. Ginley and A. J. Frank, Solid-state and electrochemical properties of polyselenophene, J. Appl. Phys., 62, 190-194 (1987).
40. S. Pu, J. Hou, J. Xu, G. Nie, S. Zhang, L. Shen and Q. Xiao, Electrosyntheses of freestanding and conducting polyselenophene films, Mater. Lett., 59, 1061-1065 (2005).
41. S. Inoue, H. Nakanishi, K. Takimiya, Y. Aso and T. Otsubo, Electrochemical and spectroscopic properties of oligoselenophenes, Synth. Met., 84, 341-342 (1997).
42. T.-T. Ong, S.-C. Ng and H. S. O. Chan, Synthesis, characterization and electrochemical properties of polybise-lenophene, Polymer, 44, 5597-5603 (2003).
43. G. Dian, G. Barbey and B. Decroix, Electrochemical synthesis of polythiophenes and polyselenophenes, Synth. Met., 13, 281-289 (1986).
44. G. Dian, N. Merlet, G. Barbey, F. Outurquin and C. Paulmier, Electrochemical polymerization of ß-substituted and β,β'-disubstituted selenophenes, J. Electroanal. Chem. Interf. Electrochem., 238, 225-237 (1987).
45. N. Merlet, G. Dian, G. Barbey, F. Outurquin and C. Paulmier, Electrochemical study of poly(3-methyl-selenophene), Synth. Met., 24, 77-80 (1988).
46. K. Yoshino, M. Onoda, Y. Manda, K. Sawada, R. Sugimoto and S. Inoue, Fusible poly(3-alkylselenophene) and its properties, Jpn. J. Appl. Phys., 28, L138-L140 (1989).
47. A. Bourahla, J. M. Saiter and C. Vautier, Electrical conductivity of polymethyl-3-selenophene, Mater. Chem. Phys., 69, 163-165 (2001).
48. C. Mahatsekake, J. M. Catel, C. G. Andrieu, M. Ebel, Y. Mollier and G. Tourillon, Synthese et etude electrochimique de poly(alkyl-3-selenophenes), Phosphorus Sulfur Silicon, 47, 35-41 (1990).
49. G. Tourillon, E. Dartyge, D. Guay, C. Mahatsekake, C. G. Andrieu, S. Bernstorff and W. Braun, Electronic properties and orientation studies of poly-3-alkylselenophene electrochemically deposited on Pt as observed by NEXAFS, J. Electrochem. Soc., 137, 1827-1832 (1990).
50. C. G. Andrieu, V. Duchenet, C. Mahatsekake, J. M. Catel, J. P. Sauve and G. Le Coustumer, Polymerization chimique et electrochimique de 3-alkyl selenophenes, Sulfur Lett., 19, 261-266 (1996).
51. L. B. Groenendaal, F. Jonas, D Freitag, H. Pielartzik and J. R. Reynolds, Poly(3,4-ethylenedioxythiophene) and its derivatives: past, present and future, Adv. Mater., 12, 481-494 (2000).
52. E. Aqad, M. V. Lakshmikantham and M. P. Cava, Synthesis of 3,4-ethylenedioxyselenophene (EDOS): a novel building block for electron-rich π-conjugated polymers, Org. Lett., 3, 4283-4285 (2001).
53. H. Nakanishi, S. Inoue and T. Otsubo, The first oligoselenophenes: synthesis and properties, Mol. Cryst. Liq. Cryst., 296, 335-348 (1997).
54. T.-C. Chung, J. H. Kaufman, A. J. Heeger and F. Wudl, Charge storage in doped poly(thiophene): optical and electrochemical studies, Phys. Rev. B, 30, 702-710 (1984).
55. G. Tourillon, D. Gourier, F. Garnier and D. Vivien, Electron spin resonance study of electrochemically generated polythiophene and derivatives, J. Phys. Chem., 88, 1049-1051 (1984).
56. H. Nakanishi, S. Inoue, Y. Aso and T. Otsubo, Molecular and crystal structures of 2,2':5',2':5',2"-quaterselenophene, Synth. Met., 101, 639 (1999).
57. V. Peulon, G. Barbey, F. Outurquin and C. Paulmier, Electrochemical synthesis and study of polyselenienylth-iophene, Synth. Met., 53, 115-126 (1993).
58. V. Peulon, G. Barbey and J.-J. Malandain, Influence of doping anion on electrochemical and physical properties of polyselenienyl thiophene polymer, Synth. Met., 82, 111-117 (1996).
59. K. Kizu, T. Maruyama and T. Yamamoto, π-Conjugated copolymers of electron-withdrawing pyridine and electron-donating selenophene, Polym. J., 27, 205-209 (1995).
60. T. Yamamoto, π-Conjugated polymers bearing electronic and optical functionalities. Preparation by organometal-lic polycondensations, properties and their applications, Bull. Chem. Soc. Jpn., 72, 621-638 (1999).
61. T. Yamamoto, Z. Zhou, T. Kanbara, M. Shimura, K. Kizu, T. Maruyama, Y. Nakamura, T. Fukuda, B.-L. Lee, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, K. Kubota and S. Sasaki, π-Conjugated donor-acceptor copolymers constituted of π-excessive and π-deficient arylene units. Optical and electrochemical properties in relation to CT structure of the polymer, J. Am. Chem. Soc., 118, 10389-10399 (1996).
62. T. Yamamoto, B.-L. Lee, I. Nurulla, T. Yasuda, I. Yamaguchi, A. Wada, C. Hirose, M. Tasumi, A. Sakamoto and E. Kobayashi, Transfer of photoenergy in π-conjugated polymers. Two types of photoluminescence that involve energy transfer along a polymer chain, J. Phys. Chem. B, 109, 10605-10610 (2005).
63. I. H. Jenkins, U. Salzner and P. G. Pickup, Conducting copolymers of pyridine with thiophene, N-methylpyrrole and selenophene, Chem. Mater., 8, 2444-2450 (1996).
64. S. Iwatsuki, M. Kubo and N. Kamei, Preparation of poly(2,5-selenophenediyl-vinylene) film by sulfonium salt method, Chem. Lett., 1551-1554 (1992).
65. S. C. Ng, H. S. O. Chan, H. H. Huang, T. T. Ong, A. Sarkar, K. Kumura, Y. Mazaki and K. Kobayashi, Poly{1,2-di(2-selinyl)ethene}, a novel electroactive polymer with reduced bandgap, J. Mater. Sci. Lett., 15, 1684-1686 (1996).
66. S. C. Ng, H. S. O. Chan, T. T. Ong, K. Kumura, Y. Mazaki and K. Kobayashi, Synthesis and characterization of poly{1,2-bis(2-seleninyl)ethene}, a novel electrically conductive polymer with diminished bandgap, Macromolecules, 31, 1221-1228 (1998).
67. M. A. Del Valle, J. Moreno, F. R. Diaz, L. H. Tagle, J. C. Bernede and Y. Tregoiiet, Synthesis and characterization of polymers derived from selenophene, J. Appl. Polym. Sci., 81, 2019-2026 (2001).
68. A. G. MacDiarmid, 'Synthetic metals': a novel role for organic polymers (Nobel Lecture), Angew. Chem. Int. Ed., 40, 2581-2590 (2001).
69. S.-C. Ng and L. Xu, Poly[4-(2-heteroaryl)benzenamines]: novel electrically conducting alternating copolymers of aniline and chalcophenes, Adv. Mater., 10, 1525-1529 (1998).
70. R. Yang, R. Tian, Q. Hou, Y. Zhang, Y. Li, W. Yang, C. Zhang and Y. Cao, Light-emitting copolymers based on fluorene and selenophene-comparative studies with its sulfur analogue: poly(fluorene-co-thiophene), J. Polym. Sci., Part A, 43, 823-836 (2005).
71. R. Yang, R. Tian, J. Yan, Y. Zhang, J. Yang, Q. Hou, W. Yang, C. Zhang and Y. Cao, Deep-red electroluminescent polymers: synthesis and characterization of new low-band-gap conjugated copolymers for light-emitting diodes and photovoltaic devices, Macromolecules, 38, 244-253 (2005).
72. T. Otsubo and K. Takimiya, Recent synthetic advances of tetrathiafulvalene-based organic conductors, Bull. Chem. Soc. Jpn., 77, 43-58 (2004).
73. R. Ketcham, A.-B. Hornfeldt and S. Gronowitz, Synthesis of tetrathiafulvalene doubly fused to the 3,4-position of selenophene, J. Org. Chem., 49, 1117-1119 (1984).
74. T. Jigami, K. Takimiya, T. Otsubo and Y. Aso, Novel selenocycle-fused TTF-type of electron donors forming conducting molecular complexes: bis(ethyleneseleno)tetrathiafulvalene (BES-TTF), diselenolotetrathiafulvalene (DS-TTF) and bis(ethyleneseleno)tetraselenafulvalene (BES-TSF), J. Org. Chem., 63, 8865-8872 (1998).
75. C. Wang, A. Ellern, J. Y. Becker and J. Bernstein, New angular molecular donor containing two tetrathiafulvalene (TTF) units fused to selenophene: synthesis, X-ray structure, cyclic voltammetry and conducting charge transfer complex with TCNQ, Adv. Mater., 7, 644-646 (1995).
76. S. Gronowitz and B. Uppstrom, On the reaction of 2,5-dihalothiophenes with tetracyanoethylene oxide, Acta Chem. Scand., B28, 981-985 (1974).
77. F. Ogura, T. Otsubo and Y. Aso, Design of novel chalcogen-containing organic metals: extensively conjugated electron donors and acceptors with reduced on-site Coulomb repulsion, Sulfur Rep., 11, 439-464 (1992).
78. F. Ogura and T. Otsubo, Conductive hetero-TCNQs, in Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, John Wiley & Sons, Ltd, Chichester, 1997, Vol. 1, Chapter 4, pp. 229-248.
79. K. Yui, Y. Aso, T. Otsubo and F. Ogura, Extensively conjugated homologues of selenophene-TCNQ as new electron acceptors, Chem. Lett., 1179-1182 (1988).
80. K. Takahashi and S. Tarutani, Novel metallic charge-transfer complexes composed of a [3]radialene type acceptor: a 1,2-bis(_p-benzoquino)-3-[2-(dicyanomethylene)-2,5-selenoquino]cyclopropane derivative, Adv. Mater., 7, 639-641 (1995).
81. K. Takahashi, K. Tomitani, T. Ise and T. Shirahata, Selenienoquinonoid-extended analogues of TTF, EDT-TTF and BEDT-TTF. New donors and their conductive complexes, Chem. Lett., 619-620 (1995).
82. 3 complexes, J. Mater. Chem., 7, 2375-2379 (1997).
83. K. Takahashi and T. Ise, 1,3-Bis(1,3-dithiol-2-ylidene)-1,3-dihydrobenzo[c]heterophenes. New fused heterocycle-extended donors and their conducting TCNQ complexes, Heterocycles, 45, 1051-1954 (1997).
84. K. Takahashi and T. Ise, Electron donors for organic conductors. Alkylenedithio derivatives of 1,3-bis(1,3-dithiol-2-ylidene)-1,3-dihydrobenzo[c]selenophene, Phosphorus Sulfur Silicon, 120-121, 415-416 (1997).
85. K. Takahashi, T. Ise, T. Mori, H. Mori and S. Tanaka, Synthesis of BEDT-BDTBS and crystal structures of its conducting cation radical salts, Chem. Lett., 1001-1002 (1996).
86. R. Gompper and H.-U. Wagner, Donor-acceptor-substituted cyclic π-electron system-probes for theories and building blocks for new materials, Angew. Chem. Int. Ed. Engl., 27, 1437-1455 (1988).
87. J. Fabian, H. Nakazumi and M. Matsuoka, Near-infrared absorbing dyes, Chem. Rev., 92, 1197-1226 (1992).
88. P. N. Prasad and B. A. Reinhardt, Is there a role for organic materials chemistry in nonlinear optics and photonics? Chem. Mater., 2, 660-669 (1990).
89. S. R. Marder and J. W. Perry, Molecular materials for second-order nonlinear optical applications, Adv. Mater., 5, 804-815 (1993).
90. R. Gompper, H.-U. Wagner and E. Kutter, Stable _p-Chinodimethane I: Synthesen und Eigenschaften, Chem. Ber., 101, 4123-4143 (1968).
91. R. Gompper and H.-U. Wagner, Der Einfuss der Anellierung auf die Fabre von Chinonmethiden, Chinodimethanen und Arylcarboniumionen, Tetrahedron Lett., 165-169 (1968).
92. S. Inoue, S. Mikami, Y. Aso, T. Otsubo, T. Wada and H. Sasabe, Donor-acceptor-substituted heteroquinoid chromophores as novel nonlinear optics, Synth. Met., 84, 395-396 (1997).
93. S. Inoue, S. Mikami, Y. Aso and T. Otsubo, Syntheses, structures and spectroscopic properties of push-pull heteroquinoid compounds, Heterocycles, 71, 253-268 (2007).
94. K. Takahashi, A. Gunji, K. Yanagi and M. Miki, Synthesis of novel heteroquaterphenoquinones and their electrochemical, structural and spectroscopic characterization, J. Org. Chem., 61, 4784-4792 (1996).
95. H. E. Katz, Recent advances in semiconductor performance and printing processes for organic transistor-based electronics, Chem. Mater., 16, 4748-4756 (2004).
96. M. M. Ling and Z. Bao, Thin film deposition, patterning and printing in organic thin film transistors, Chem. Mater., 16, 4824-4840 (2004).
97. Y. Sun, Y. Liu and D. Zhu, Advances in organic field-effect transistors, J. Mater. Chem., 15, 53-65 (2005).
98. M. Muccini, A bright future for organic field-effect transistor, Nat. Mater., 5, 605-613 (2006).
99. J. E. Anthony, Functionalized acenes and heteroacenes for organic electronics, Chem. Rev., 106, 5028-5048 (2006).
100. K. Takimiya, Y. Kunugi and T. Otsubo, Development of new semiconducting materials for durable high-performance air-stable organic field-effect transistors, Chem. Lett., 36, 578-583 (2007).
101. Y. Kunugi, K. Takimiya, K. Yamane, K. Yamashita, Y. Aso and T. Otsubo, Organic field-effect transistor using oligoselenophene as an active layer, Chem. Mater., 15, 6-7 (2003).
102. H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig and D. M. de Leeuw, Two-dimensional charge transport in self-organized, high-mobility conjugated polymers, Nature, 401, 685-688 (1999).
103. D. J. Crouch, P. J. Skabara, J. E. Lohr, J. J. W. McDouall, M. Heeney, I. McCulloch, D. Sparrowe, M. Shkunov, S. J. Coles, P. N. Horton and M. B. Hursthouse, Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: synthesis, characterization and application in organic field-effect transistor, Chem. Mater., 17, 6567-6578 (2005).
104. Y. M. Kim, E. Lim, I.-N. Kang, B.-J. Jung, J. Lee, B. W. Koo, L.-M. Do and H.-K. Shim, Solution-processable field-effect transistor using a fluorene-and selenophene-based copolymer as an active layer, Macromolecules, 39, 4081-4085 (2006).
105. H. Meng, Z. Bao, A. J. Lovinger, B.-C. Wang and A. M. Mujsce, High field-effect mobility oligofluorene derivatives with high environmental stability, J. Am. Chem. Soc., 123, 9214-9215 (2001).
106. B. Ong, Y. Wu, L. Jiang, P. Liu and K. Murti, Polythiophene-based field-effect transistors with enhanced air stability, Synth. Met., 142, 49-52 (2004).
107. Y. Wu, Y. Li, S. Gardner and B. S. Ong, Indolo[3,2-b]carbazole-based thin-film transistors with high mobility and stability, J. Am. Chem. Soc., 127, 614-618 (2005).
108. M. Heeney, C. Bailey, K. Genevicius, M. Shkunov, D. Sparrowe, S. Tierney and I. McCulloch, Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene, J. Am. Chem. Soc., 127, 1078-1079 (2005).
109. K. Takimiya, Y. Kunugi, Y. Konda, N. Niihara and T. Otsubo, 2,6-Diphenylbenzo[1,2-fc:4,5-fc']dichal-cogenophenes: a new class of high-performance semiconductors for organic field-effect transistors, J. Am. Chem. Soc., 126, 5084-5085 (2004).
110. K. Takimiya, Y. Kunugi, Y. Konda, H. Ebata, Y. Toyoshima and T. Otsubo, 2,7-Diphenyl[1] benzoselenopheno[3,2-b][1]benzoselenophene as a stable organic semiconductor for a high-performance field-effect transistor, J. Am. Chem. Soc., 128, 3044-3050 (2006).
111. N. P. Buu-Hoi, M. Mangane, M. Renson and L. Cristiaens, Thiophene derivatives. XIX. Behavior of benzo[b]selenophenes under electron impact; comparison with benzo[b]thiophenes, J. Chem. Soc. B, 971-973 (1969).
112. M. Renson, Recent aspects of the chemistry of benzo[b]selenophene and benzo[b]tellurophene, Chem. Scr., 8A, 29-38 (1975).
113. A. Bugge, The synthesis of seleno[2,3-fc]thiophene, Acta Chem. Scand., 23, 1823-1824 (1969).
114. S. Gronowitz, A. Konar and A.-B. Hornfeldt, On the reaction between acetylene and selenium, Chem. Scr., 10, 159-164 (1976).
115. S. Gronowitz and A. Konar, Nonclassical selenoloselenophenes, Chem. Commun., 163-164 (1977).
116. A. Konar and S. Gronowitz, Selenolo[3,4-b]selenophene-the third 'classical' selenophene, Tetrahedron, 36, 3317-3323 (1980).
117. H. Sashida and S. Yasuike, Studies on tellurium-containing heterocycles 7. A simple one-pot synthesis of [1]benzotelluro[3,2-b][1]benzotellurophenes and its selenium and sulfur analogs from 2,2'-dibromo-diphenylacetylene, J. Heterocycl. Chem., 35, 725-726 (1988).
118. H. Sashida, K. Sadamori and T. Tsuchiya, A convenient one-pot preparation of benzo[b]-tellurophenes,-selenophenes and-thiophenes from o-bromoethynylbenzenes, Synth. Commun., 28, 713-727 (1998).
119. K. Takimiya, Y. Konda, H. Ebata, N. Niihara and T. Otsubo, Facile synthesis, structure and properties of benzo[1,2-fc:4,5-fc']dichalcogenophenes, J. Org. Chem., 70, 10569-10571 (2005).
120. T. Okamoto, K. Kudoh, A. Wakamiya and S. Yamaguchi, General synthesis of thiophene and selenophene-based heteroacenes, Org. Lett., 7, 5301-5304 (2005).
121. K. Takimiya, Y. Konda, H. Ebata, T. Otsubo and Y. Kunugi, Organic field-effect transistors based on 2,6-dipenylbenzo[1,2-b:5,4-b']-dithiophene and-diselenophene (iso-DPh-BDXs), Mol. Cryst. Liq. Cryst., 455, 361-365 (2006).
122. R. Zeis, C. Kloc, K. Takimiya, Y. Kunugi, Y. Konda, N. Niihara and T. Otsubo, Single-crystal field-effect transistors based on organic selenium-containing semiconductor, Jpn. J. Appl. Phys., 44, 3712-3714 (2005).
123. T. Yamamoto and K. Takimiya, Facile synthesis of highly π-extended heteroarenes, dinaphtho[2,3-b:2',3'-/] chalcogenopheno[3,2-b]chalcogenophenes and their application to field-effect transistors, J. Am. Chem. Soc., 129, 2224-2225 (2007).
124. C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J.-L. Bredas, P. C. Ewbank and K. R. Mann, Introduction to organic thin film transistors and design of n-channel organic semiconductors, Chem. Mater., 16, 4436-4451 (2004).
125. Y. Kunugi, K. Takimiya, Y. Toyoshima, K. Yamashita, Y. Aso and T. Otsubo, Vapour deposited films of quinoidal biselenophene and bithiophene derivatives as active layers of n-channel organic field-effect transistors, J. Mater. Chem., 14, 1367-1369 (2004).
126. K. Takimiya, Y. Kunugi, H. Ebata and T. Otsubo, Molecular modification of 2,6-diphenylbenzo [1,2-b:4,5-b']dichalcogenophenes by introduction of strong electron-withdrawing groups: conversion from p-to n-channel OFET materials, Chem. Lett., 35, 1200-1201 (2006).
127. S. Jaradat, N. W. Roberts, Y. Wang, L. S. Hirst and H. F. Gleeson, Remarkably wide four-layer smectic phases in mixtures of liquid crystals and highly chiral dopants, J. Mater. Chem., 16, 3753-3761 (2006).
128. H. Ohishi, M. Tanaka, H. Kageyama and Y. Shirota, Amorphous molecular materials with high carrier mobilities: thiophene-and selenophene-containing tris(oligoarylenyl)amines, Chem. Lett., 33, 1266-1267 (2004).
129. D. G. Hilmey, M. Abe, M. I. Nelen, C. E. Stilts, G. A. Baker, S. N. Baker, F. V. Bright, S. R. Davies, S. O. Gollnick, A. R. Oseroff, S. L. Gibson, R. Hilf and M. R. Detty, Water-soluble, core-modified porphyrins as novel, longer-wavelength-absorbing sensitizers for photodynamic therapy. II. Effects of core heteroatoms and meso-substituents on biological activity, J. Med. Chem., 45, 449-461 (2002).
130. H.-S. Shiah, W.-S. Lee, S.-H. Juang, P.-C. Hong, C.-C. Lung, C.-J. Chang, K.-M. Chou and J.-Y. Chang, Mitochondria-mediated and p53-associated apoptosis induced in human cancer cells by a novel selenophene derivative, D-501036, Biochem. Pharm., 73, 610-619 (2007).