Solid-emissive BODIPY derivatives: Design, synthesis and applications

Current Organic Chemistry

Volumn 16, Issue 24, 2012, Pages 2970-2981

  Xiao, Shuzhang ^a   Cao, Qiong ^a   Dan, Feijun ^a  

^a CHINA THREE GORGES UNIVERSITY   (China)

Author keywords

Aggregate induced emission; BODIPY; Chromophore; Fluorescence; Solid emission; Steric effect; Supramolecular chemistry

Indexed keywords

CHEMICAL STABILITY; FLUORESCENCE; ORGANIC LIGHT EMITTING DIODES (OLED); SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

AGGREGATE-INDUCED EMISSION; BODIPY; DESIGN APPLICATIONS; DESIGN SYNTHESIS; EMISSIVE MATERIALS; LIGHTEMITTING DIODE; ORGANIC LIGHT-EMITTING; PHOTOPHYSICAL PROPERTIES; SOLID EMISSIONS; STERIC EFFECT;

CHROMOPHORES;

EID: 84872577090     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212804546796     Document Type: Review

References (91)

1. Zaumseil, J.; Sirringhaus, H. Electron and ambipolar transport in organic field-effect transistors. Chem. Rev., 2007, 107, 1296-1323.
2. Samuel, I.D.W.; Turnbull, G.A. Organic semiconductor lasers. Chem. Rev., 2007, 107, 1272-1295.
3. Thomas, S.W.; Joly, G.D.; Swager, T.M. Chemical sensors based on amplifying fluorescent conjugated polymers. Chem. Rev., 2007, 107, 1339-1386.
4. Basabe-Desmonts, L.; Reinhoudt, D.N.; Crego-Calama, M. Design of fluorescent materials for chemical sensing. Chem. Soc. Rev., 2007, 36, 993-1017.
5. Martinez-Manez, R.; Sancenon, F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev., 2003, 103, 4419-4476.
6. de Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev., 1997, 97, 1515-1566.
7. Cicoira, F.; Santato, C. Organic light emitting field effect transistors: advances and perspectives. Adv. Funct. Mater., 2007, 17, 3421-3434.
8. Kumar, N.S.S.; Varghese, S.; Rath, N.P.; Das, S. Solid state optical properties of 4-alkoxy-pyridine butadiene derivatives: reversible thermal switching of luminescence. J. Phys. Chem. C, 2008, 112, 8429-8437.
9. Wong, K.T.; Chien, Y.Y.; Chen, R.T.; Wang, C.F.; Lin, Y.T.; Chiang, H.H.; Hsieh, P.Y.; Wu, C.C.; Chou, C.H.; Su, Y.O.; Lee, G.H.; Peng, S.M. Ter(9,9-diarylfluorene)s: highly efficient blue emitter with promising electrochemical and thermal stability. J. Am. Chem. Soc., 2002, 124, 11576-11577.
10. Chiang, C. L; Wu, M.F.; Dai, D.C.; Wen, Y.S.; Wang, J.K.; Chen, C.T. Redemitting fluorenes as efficient emitting hosts for non-doped, organic redlight-emitting diodes. Adv. Funct. Mater., 2005, 15, 231-238.
11. Wilson, J.N.; Smith, M.D.; Enkelmann, V.; Bunz, U.H.F. Cruciform π-systems: effect of aggregation on emission. Chem. Commun., 2004, 1700-1701.
12. Ortiz, A.; Flora, W.H.; D'Ambruoso, G.D.; Armstrong, N.R.; McGrath, D.V. Dendritic incorporation of quinacridone: solubility, aggregation, electrochemistry, and solid-state luminescence. Chem. Commun., 2005, 444-446.
13. Zhang, S.W.; Swager, T.M. Fluorescent detection of chemical warfare agents: functional group specific ratiometric chemosensors. J. Am. Chem. Soc., 2003, 125, 3420-3421.
14. Jakubiak, R.; Bao, Z. N; Rothberg, L. Dendritic sidegroups as threedimensional barriers to aggregation quenching of conjugated polymer fluorescence. Synth. Met., 2000, 114, 61-64.
15. Langhals, H.; Ismael, R.; Yuruk, O. Persistent fluorescence of perylene dyes by steric inhibition of aggregation. Tetrahedron, 2000, 56, 5435-5441.
16. Sreejith, S.; Divya, K.P.; Ajayaghosh, A. Detection of zinc ions under aqueous conditions using chirality assisted solid-state fluorescence of a bipyridyl based fluorophore. Chem. Commun., 2008, 2903-2905.
17. Luo, J.D.; Xie, Z. L; Lam, J.W.Y.; Cheng, L.; Chen, H.Y.; Qiu, C.F.; Kwok, H.S.; Zhan, X.W.; Liu, Y.Q.; Zhu, D.B.; Tang, B.Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun., 2001, 1740-1741.
18. Tang, B.Z.; Zhan, X.W.; Yu, G.; Lee, P.P.S.; Liu, Y.Q.; Zhu, D.B. Efficient blue emission from siloles. J. Mater. Chem., 2001, 11, 2974-2978.
19. Chen, J.W.; Law, C.C.W.; Lam, J.W.Y.; Dong, Y.P.; Lo, S.M.F.; Williams, I.D.; Zhu, D.B.; Tang, B.Z. Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles. Chem. Mater., 2003, 15, 1535-1546.
20. An, B.K.; Kwon, S.K.; Jung, S.D.; Park, S.Y. Enhanced emission and its switching in fluorescent organic nanoparticles. J. Am. Chem. Soc., 2002, 124, 14410-14415.
21. 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. Mater., 2002, 14, 1332-1339.
22. He, F.; Xu, H.; Yang, B.; Duan, Y.; Tian, L.L.; Huang, K.K.; Ma, Y.G.; Liu, S.Y.; Feng, S.H.; Shen, J.C. Oligomeric phenylenevinylene with cross dipole arrangement and amorphous morphology: enhanced solid-state luminescence efficiency and electroluminescence performance. Adv. Mater., 2005, 17, 2710-2714.
23. Bilge, A.; Zen, A.; Forster, M.; Li, H.B.; Galbrecht, F.; Nehls, B.S.; Farrell, T.; Neher, D.; Scherf, U. Swivel-cruciform oligothiophene dimmers. J. Mater. Chem., 2006, 16, 3177-3182.
24. Xie, Z.Q.; Yang, B.; Cheng, G.; Liu, L. L; He, F.; Shen, F.Z.; Ma, Y.G.; Liu, S.Y. Supramolecular interactions induced fluorescence in crystal: anomalous emission of 2,5-diphenyl-1,4-distyrylbenzene with all cis double bonds. Chem. Mater., 2005, 17, 1287-1289.
25. Xie, Z.Q.; Liu, L.L.; Yang, B.; Yang, G.D.; Ye. L.; Li, M.; Ma, Y.G. Polymorphism of 2,5-diphenyl-1,4-distyrylbenzene with two cis double bonds: the essential role of aromatic ch/π hydrogen bonds. Cryst. Growth. Des., 2005, 5, 1959-1964.
26. Feast, W.J.; Lovenich, P.W.; Puschmann, H.; Taliani, C. Synthesis and structure of 4,4'-bis(2,3,4,5,6-pentafluorostyryl)stilbene, a self-assembling J aggregate based on aryl-fluoroaryl interactions. Chem. Commun., 2001, 505-506.
27. Kaiser, T.E.; Wang, H.; Stepanenko, V.; Wurthner, F. Supramolecular construction of fluorescent J-aggregates based on hydrogen-bonded perylene dyes. Angew. Chem. Int. Ed., 2007, 46, 5541-5544.
28. Zhao, C.H.; Wakamiya, A.; Inukai, Y.; Yamaguchi, S. Highly emissive organic solids containing 2,5-diboryl-1,4-phenylene unit. J. Am. Chem. Soc., 2006, 128, 15934-15935.
29. Shimizu, M.; Takeda, Y.; Higashi, M.; Hiyama, T. 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: minimal fluorophores exhibiting highly efficient emission in the solid state. Angew. Chem. Int. Ed., 2009, 48, 3653-3656.
30. Sato, T.; Jiang, D.L.; Aida, T. A blue-luminescent dendritic rod: poly(phenyleneethynylene) within a light-harvesting dendritic envelope. J. Am. Chem. Soc., 1999, 121, 10658-10659.
31. Loudet, A.; Burgess, K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem. Rev., 2007, 107, 4891-4932.
32. Kim, H.N.; Ren, W.X.; Kim, J.S.; Yoon, J. Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chem. Soc. Rev., 2012, 41, 3210-3244.
33. Boens, N.; Leen, V.; Dehaen, W. Fluorescent indicators based on BODIPY. Chem. Soc. Rev., 2012, 41, 1130-1172.
34. Karolin, J.; Johansson, L.B.A.; Strandberg, L.; Ny. T. Fluorescence and absorption spectroscopic properties of dipyrrometheneboron difluoride (BODIPY) derivatives in liquids, lipid membranes, and proteins. J. Am. Chem. Soc., 1994, 116, 7801-7806.
35. Golovkova, T.A.; Kozlov, D.V.; Neckers, D.C. Synthesis and properties of novel fluorescent switches. J. Org. Chem., 2005, 70, 5545-5549.
36. Ozdemir, T.; Atilgan, S.; Kutuk, I.; Yildirim, L.T.; Tulek, A.; Bayindir, M.; Akkaya, E.U. Solid-state emissive BODIPY dyes with bulky substituents as spacers. Org. Lett., 2009, 11, 2105-2107.
37. Bandichhor, R.; Thivierge, C.; Bhuvanesh, N.S.P.; Burgess, K. 4,4-Difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene. Acta Cryst, E, 2006, 62, O4310-O4311.
38. Wang, D.C.; Wang, H.P.; Gao, S.; Zhang, T.Y.; Peng, X.J. 4,4-Difluoro-8-methyl-4-bora-3a,4a-diaza-s-indacene. Acta Cryst, E, 2007, 63, O2238-O2239.
39. Zhang, D. K; Wen, Y. G; Xiao, Y.; Yu, G.; Liu, Y. Q; Qian, X.H. Bulky 4-tritylphenylethynyl substituted boradiazaindacene: pure red emission, relatively large Stokes shift and inhibition of self-quenching. Chem. Commun., 2008, 4777-4779.
40. Fu, G.L.; Pan, H.; Zhao, Y.H.; Zhao, C.H. Solid-state emissive triarylboranebased BODIPY dyes: photophysical properties and fluorescent sensing for fluoride and cyanide ions. Org. Biomol. Chem., 2011, 9, 8141-8146.
41. Lu, H.; Wang, Q.H.; Gai, L.Z.; Li, Z.F.; Deng, Y.; Xiao, X.Q.; Lai, G.Q.; Shen, Z. Tuning the solid-state luminescence of BODIPY derivatives with bulky arylsilyl groups: synthesis and spectroscopic properties. Chem. Eur. J., 2012, 18, 7852-7861.
42. Schmidt, E.Y.; Zorina, N.V.; Dvorko, M.Y.; Protsuk, N.I.; Belyaeva, K.V.; Clavier, G.; Meallet-Renault, R.; Vu, T.T.; Mikhaleva, A.I.; Trofimov, B.A. A general synthetic strategy for the design of new BODIPY fluorophores based on pyrroles with polycondensed aromatic and metallocene substituents. Chem. Eur. J., 2011, 17, 3069-3073.
43. Schmidt, E.Y.; Trofimov, B.A.; Mikhaleva, A.I.; Zorina, N.V.; Protzuk, N.I.; Petrushenko, K.B.; Ushakov, I.A.; Dvorko, M.Y.; Meallet-Renault, R.; Clavier, G.; Vu, T.T.; Tran, H.T.T.; Pansu, R.B. Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene). Chem. Eur. J., 2009, 15, 5823-5830.
44. Vu, T.T.; Badre, S.; Dumas-Verdes, C.; Vachon, J.J.; Julien, C.; Audebert, P.; Senotrusova, E.Y.; Schmidt, E.Y.; Trofimov, B.A.; Pansu, R.B.; Clavier, G.; Meallet-Renault, R. New hindered BODIPY derivatives: solution and amorphous state fluorescence properties. J. Phys. Chem. C, 2009, 113, 11844-11855.
45. 2)-2,2'-bidipyrrins (bisbodipys): highly fluorescent BODIPY dimers with large stokes shifts. Chem. Eur. J., 2008, 14, 2976-2983.
46. Xi, H.; Yuan. C.X.; Li, Y.X.; Liu, Y.; Tao, X.T. Crystal structures and solidstate fluorescence of BODIPY dyes based on Λ-shaped Troger's base. CrystEngComm, 2012, 14, 2087-2093.
47. 2 complexes. Tetrahedron Lett., 2010, 51, 6195-6198.
48. Goze, C.; Ulrich, G.; Mallon, L.J.; Allen, B.D.; Harriman, A.; Ziessel, R. Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center. J. Am. Chem. Soc., 2006, 128, 10231-10239.
49. Araneda, J.F.; Piers, W.E.; Heyne, B.; Parvez, M.; McDonald, R. High Stokes shift anilido-pyridine boron difluoride dyes. Angew. Chem. Int. Ed., 2011, 50, 12214-12217.
50. Zhou, Y.; Xiao, Y.; Li, D.; Fu, M.Y.; Qian, X.H. Novel fluorescent fluorineboron complexes: synthesis, crystal structure, photoluminescence, and electrochemistry properties. J. Org. Chem., 2008, 73, 1571-1574.
51. Zhou, Y.; Xiao, Y.; Chi, S.M.; Qian, X.H. Isomeric boron-fluorine complexes with donor-acceptor architecture: strong solid/liquid fluorescence and large Stokes shift. Org. Lett., 2008, 10, 633-636.
52. Feng, J.Q.; Wang, D.L.; Wang, S.Q.; Zhang, L.L.; Li, X.Y. Synthesis and properties of novel perylenetetracarboxylic diimide derivatives fused with BODIPY units. Dyes Pigm., 2011, 89, 23-28.
53. 2 complexes with 1,3-diketone ligands. Tetrahedron, 2007, 63, 9354-9358.
54. Zhang, G.Q.; Lu, J.W.; Sabat, M.; Fraser, C.L. Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone. J. Am. Chem. Soc., 2010, 132, 2160-2162.
55. Mao, M.F.; Xiao, S.Z.; Yi, T.; Zou, K. Synthesis and characterization of novel fluorescent BOPIM dyes with large Stokes shift. J. Fluorine Chem., 2011, 132, 612-616.
56. Mao, M.F.; Zhang, R.H.; Xiao, S.Z.; Zou, K. Synthesis, crystal structures and photophysical properties of dibromo-2-(2-pyridyl)imidazole and its corresponding boron-fluorine complex. J. Coord. Chem., 2011, 64, 3303-3310.
57. Mao, M.F.; Xiao, S.Z.; Li, J.F.; Zou, Y.; Zhang, R.H.; Pan, J.R.; Dan, F.J.; Zou, K.; Yi, T. Solid-emissive borone-fuorine derivatives with large stokes shift. Tetrahedron, 2012, 68, 5037-5041.
58. Cao, Q.; Xiao, S.Z.; Mao, M.F.; Chen, X.H.; Wang, S.; Li, L.; Zou, K. Structure-property correlation of solid-emissive boron-fluorine derivatives. J. Organomet. Chem., 2012, 717, 147-151.
59. 2 complex. Org. Lett., 2010, 12, 4010-4013.
60. Frath, D.; Azizi, S.; Ulrich, G.; Retailleau, P.; Ziessel, R. Facile synthesis of highly fluorescent boranil complexes. Org. Lett., 2011, 13, 3414-3417.
61. Kubota, Y.; Hara, H.; Tanaka, S.; Funabiki, K.; Matsui, M. Synthesis and fluorescence properties of novel pyrazine-boron complexes bearing a β-iminoketone ligand. Org. Lett., 2011, 13, 6544-6547.
62. Yoshino, J.; Furuta, A.; Kambe, T.; Itoi, H.; Kano, N.; Kawashima, T.; Ito, Y.; Asashima, M. Intensely fluorescent azobenzenes: synthesis, crystal structures, effects of substituents, and application to fluorescent vital stain. Chem. Eur. J., 2010, 16, 5026-5035.
63. 2 complexes bearing (2-quinolin-2-yl) phenol ligands. J. Fluorine Chem., 2012, 137, 93-98.
64. Feng, J.Q.; Liang, B.L.; Wang, D.L.; Xue, L.; Li, X.Y. Novel fluorescent dyes with fused perylene tetracarboxlic diimide and BODIPY analogue structures. Org. Lett., 2008, 10, 4437-4440.
65. Santra, M.; Moon, H.; Park, M.H.; Lee, T.W.; Kim, Y.K.; Ahn, K.H. Dramatic substituent effects on the photoluminescence of boron complexes of 2-(benzothiazol-2-yl)phenols. Chem. Eur. J., 2012, 18, 9886-9893.
66. Xie, L.J.; Chen, Y.H.; Wu, W.T.; Guo, H.M.; Zhao, J.Z.; Yu, X.R. Fluorescent coumarin derivatives with large stokes shift, dual emission and solid state luminescent properties: An experimental and theoretical study. Dyes Pigm., 2012, 92, 1361-1369.
67. Camerel, F.; Bonardi, L.; Schmutz, M.; Ziessel, R. Highly luminescent gels and mesogens based on elaborated borondipyrromethenes. J. Am. Chem. Soc., 2006, 128, 4548-4549.
68. Camerel, F.; Bonardi, L.; Ulrich, G.; Charbonniere, L.; Donnio, B.; Bourgogne, C.; Guillon, D.; Retailleau, P.; Ziessel, R. Self-assembly of fluorescent amphipathic borondipyrromethene scaffoldings in mesophases and organogels. Chem. Mater., 2006, 18, 5009-5021.
69. Ziessel, R.; Bonardi, L.; Retailleau, P.; Camerel, F. New difluoroboradiazaindacene shaped with gallate platforms. C. R. Chimie., 2008, 11, 716-733.
70. Zhang, X.F.; Lu, R.; Jia, J.H.; Liu, X.L.; Xue, P.C.; Xu, D.F.; Zhou, H.P. Organogel based on beta-diketone-boron difluoride without alkyl chain and H-bonding unit directed by optimally balanced pi-pi interaction. Chem. Commun., 2010, 8419-8421.
71. Camerel, F.; Ulrich, G.; Barbera, J.; Ziessel. R. Ionic self-assembly of ammonium-based amphiphiles and negatively charged bodipy and porphyrin luminophores. Chem. Eur. J., 2007, 13, 2189-2200.
72. Olivier, J.H.; Camerel, F.; Ulrich, G.; Barbera, J.; Ziessel, R. Luminescent ionic liquid crystals from self-assembled BODIPY disulfonate and imidazolium frameworks. Chem. Eur. J. 2010, 16, 7134-7142.
73. Zhao, Z.J.; Wang, Z.M.; Lu, P.; Chan, C.Y.K.; Liu, D.D.; Lam, J.W.Y.; Sung, H.H.Y.; Williams, I.D.; Ma, Y.G.; Tang, B.Z. Structural modulation of solid-state emission of 2,5-bis(trialkylsilylethynyl)-3,4-diphenylsiloles. Angew. Chem. Int. Ed., 2009, 48, 7608-7611.
74. Zhao, Z.J.; Lam, J.W.Y.; Tang, B.Z. Aggregation-induced emission of tetraarylethene luminogens. Curr. Org. Chem., 2010, 14, 2109-2132.
75. Hu, R.R.; Lager, E.; Aguilar-Aguilar, A.; Liu, J.Z.; Lam, J.W.Y.; Sung, H.H.Y.; Williams, I.D.; Zhong, Y.C.; Wong, K.S.; Pena-Cabrera, E.; Tang, B.Z. Twisted intramolecular charge transfer and aggregation-induced emission of BODIPY derivatives. J. Phys. Chem. C, 2009, 113, 15845-15853.
76. 2-hydrazone (BODIHY) complexes. Chem. Sci., 2012, 3, 610-613.
77. Zhang, Z.Y.; Xu, B.; Su, J.H.; Shen, L.P.; Xie, Y.S.; Tian, H. Color-tunable solid-state emission of 2,2'-biindenyl-based fluorophores. Angew. Chem. Int. Ed. 2011, 50, 11654-11657.
78. Benniston, A.C.; Copley, G.; Harriman, A.; Rewinska, D.B.; Harrintgon, R.W.; Clegg, W. A donor acceptor molecular dyad showing multiple electronic energy-transfer processes in crystalline and amorphous states. J. Am. Chem. Soc., 2008, 130, 7174-7175.
79. Nagata, Y.; Otaka, H.; Chujo, Y. Synthesis of new main-chain-type organoboron quinolate polymer linked on quinolate ligand. Macromolecules, 2008, 41, 737-740.
80. Nagata, Y.; Chujo, Y. Synthesis of methyl-substituted main-chain-type organoboron quinolate polymers and their emission color tuning. Macromolecules, 2008, 41, 2809-2813.
81. Nagata, Y.; Chujo, Y. Main-chain-type organoboron quinolate polymers: synthesis and photoluminescence properties. Macromolecules, 2007, 40, 6-8.
82. Nagata, Y.; Chujo, Y. Main-chain-type N, N'-chelate organoboron aminoquinolate polymers: synthesis, luminescence, and energy transfer behavior. Macromolecules, 2008, 41, 3488-3492.
83. Nagai, A.; Kokado, K.; Nagata, Y.; Chujo, Y. 1,3-Diketone-based organoboron polymers: emission by extending ė-conjugation along a polymeric ligand. Macromolecules, 2008, 41, 8295-8298.
84. Zhu, M.; Jiang, L.; Yuan, M.J.; Liu, X.F.; Ouyang, C.B.; Zheng, H.Y.; Yin, X.D.; Zuo, Z.C.; Liu, H.B.; Li, Y.L. Efficient tuning nonlinear optical properties: synthesis and characterization of a series of novel poly(aryleneethynylene)s co-containing BODIPY. J. Polym. Sci. A, 2008, 46, 7401-7410.
85. Qin, Y.; Kiburu, I.; Shah, S.; Jakle, F. Synthesis and characterization of organoboron quinolate polymers with tunable luminescence properties. Macromolecules, 2006, 39, 9041-9048.
86. Qin, Y.; Pagba, C.; Piotrowiak, P.; Jakle, F. Luminescent organoboron quinolate polymers. J. Am. Chem. Soc., 2004, 126, 7015-7018.
87. Zhang, G.Q.; Chen, J.B.; Payne, S.J.; Kooi, S.E.; Demas, J.N.; Fraser, C.L. Multi-emissive difluoroboron dibenzoylmethane polylactide exhibiting intense fluorescence and oxygen-sensitive room-temperature phosphorescence. J. Am. Chem. Soc., 2007, 129, 8942-8943.
88. Pfister, A.; Zhang, G.Q.; Zareno, J.; Horwitz, A.F.; Fraser, C.L. Boron polylactide nanoparticles exhibiting fluorescence and phosphorescence in aqueous medium. ACS Nano, 2008, 2, 1252-1258.
89. Nagai, A.; Kokada, K.; Miyake, J.; Chujo, Y. Highly luminescent nanoparticles: self-assembly of well-defined block copolymers by π-π stacked BODIPY dyes as only a driving force. Macromolecules, 2009, 42, 5446-5452.
90. Nagai, A.; Yoshii, R.; Otsuka, T.; Kokado, K.; Chujo, Y. BODIPY-based chain transfer agent: reversibly thermoswitchable luminescent gold nanoparticle stabilized by BODIPY-terminated water-soluble polymer. Langmuir, 2010, 26, 15644-15649.
91. Ziessel, R.; Ulrich, G.; Harriman, A.; Alamiry, M.A.H.; Stewart, B.; Retailleau, P. Solid-state gas sensors developed from functional difluoroboradiazaindacene dyes. Chem. Eur. J., 2009, 15, 1359-1369.