Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 231, Issue 1, 2012, Pages 51-59

  Li, Yilin ^a,b   Scudiero, Louis ^c   Ren, Tianhui ^a   Dong, Wen Ji ^b  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b Washington State University   (United States)

^c WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

Benzothiadiazole; DFT; ICT; Large Stokes shift; Wavelength shifting materials

Indexed keywords

EID: 84862817559     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2012.01.011     Document Type: Article

References (38)

1. S.R. Forrest, and M.E. Thompson Introduction: organic electronics and optoelectronics Chem. Rev. 107 2007 923 925 (Pubitemid 46736531)
2. A.C. Grimsdale, K.L. Chan, R.E. Martin, P.G. Jokisz, and A.B. Holmes Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices Chem. Rev. 109 2009 897 1091
3. Y.J. Cheng, S.H. Yang, and C.S. Hsu Synthesis of conjugated polymers for organic solar cell applications Chem. Rev. 109 2009 5868 5923
4. P. Heremans, D. Cheyns, and B.P. Rand Strategies for increasing the efficiency of heterojunction organic solar cells: material selection and device architecture Acc. Chem. Res. 42 2009 1740 1747
5. N. Martin, L. Sanchez, M.A. Herranz, B. Illescas, and D.M. Guldi Electronic communication in tetrathiafulvalene (TTF)/C60 systems: toward molecular solar energy conversion materials? Acc. Chem. Res. 40 2007 1015 1024
6. S.W. Thomas III, G.D. Joly, and T.M. Swager Chemical sensors based on amplifying fluorescent conjugated polymers Chem. Rev. 107 2007 1339 1386 (Pubitemid 46736542)
7. E. Espi, A. Salmeron, A. Fontecha, Y. Garcia, and A.I. Real Plastic films for agricultural applications J. Plastic Film & Sheeting 22 2006 85 102
8. E. Klampaftis, D. Ross, K.R. Mclntosh, and B.S. Richards Enhancing the performance of solar cells via luminescent down-shifting of the incident spectrum: a review Sol. Energy Mater. Sol. Cells 93 2009 1182 1194
9. B.S. Richards, and K.R. Mclntosh Overcoming the poor short wavelength spectral responses of CdS/CdTe photovoltaic modules via luminescence down-shifting: ray-tracing simulations Prog. Photovoltaics 15 2007 27 34 (Pubitemid 46133103)
10. 2+ ions in living cells Angew. Chem. Int. Ed. 47 2008 8025 8029
11. R.E. Martin, and F. Diederich Linear monodisperse (-conjugated oligomers: model compounds for polymers and more Angew. Chem. Int. Ed. 38 1999 1350 1377
12. K.C. Moss, K.N. Bourdakos, V. Bhalla, K.T. Kamtekar, M.R. Bryce, M.A. Fox, H.L. Vaughan, F.B. Dias, and A.P. Monkman Tuning the intramolecular charge transfer emission from deep blue to green in ambipolar systems based on dibenzothiophene S,S-dioxide by manipulation of conjugation and strength of the electron donor units J. Org. Chem. 75 2010 6771 6781
13. J.L. Segura, and N. Martin Functionalized oligoarylenes as building blocks for new organic materials J. Mater. Chem. 10 2000 2403 2435
14. D.P. Hagberg, T. Marinado, K.M. Karlsson, K. Nonomura, P. Qin, G. Boschloo, T. Brinck, A. Hagfeldt, and L. Sun Tuning the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells J. Org. Chem. 72 2007 9550 9556 (Pubitemid 350231800)
15. X. Tang, W. Liu, J. Wu, C.S. Lee, J. You, and P. Wang Synthesis, crystal structures, and photophysical properties of triphenylamine-based multicyano derivatives J. Org. Chem. 75 2010 7273 7278
16. W. Lin, L. Yuan, Z. Cao, Y. Feng, and J. Song Through-bond energy transfer cassettes with minimal spectral overlap between the donor emission and acceptor absorption: coumarin-rhodamine dyads with large pseudo-Stokes shifts and emission shifts Angew. Chem. Int. Ed. 49 2010 375 379
17. C.J. Brabec, C. Winder, N.S. Sariciftci, J.C. Hummelen, A. Dhanabalan, P.A. van Hal, and R.A. Janssen A low-bandgap semiconducting polymer for photovoltaic devices and infrared emitting diodes Adv. Funct. Mater. 12 2002 709 712 (Pubitemid 35354532)
18. F.L. Zhang, A. Gadisa, O. Inganas, M. Svensson, and M.R. Andersson Influence of buffer layers on the performance of polymer solar cells Appl. Phys. Lett. 84 2004 3906 3908
19. M. Velusamy, K.R.J. Thomas, J.T. Lin, Y.-C. Hsu, and K.-C. Ho Organic dyes incorporating low-band-gap chromophores for dye-sensitized solar cells Org. Lett. 7 2005 1899 1902 (Pubitemid 40732008)
20. D. Deng, Y. Yang, J. Zhang, C. He, M. Zhang, Z.-G. Zhang, Z. Zhang, and Y. Li Triphenylamine-containing linear D-A-D molecules with benzothiadiazole as acceptor unit for bulk-heterojunction organic solar cells Organic Electronics 12 2011 614 622
21. J.-Z. Cheng, C.-C. Lin, P.-T. Chou, A. Chaskar, and K.-T. Wong Fluorene as the (-spacer for new two-photon absorption chromophores Tetrahedron 67 2011 734 739
22. A Guide to Recording Fluorescence Quantum Yields, Jobin Yvon Ltd.
23. Gaussian 09, Revision A.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G., Scalmani, V., Barone, B., Mennucci, G. A. Petersson, H., Nakatsuji, M., Caricato, X., Li, H. P. Hratchian, A. F. Izmaylov, J., Bloino, G., Zheng, J. L. Sonnenberg, M., Hada, M., Ehara, K., Toyota, R., Fukuda, J., Hasegawa, M., Ishida, T., Nakajima, Y., Honda, O., Kitao, H., Nakai, T., Vreven, J. A. Montgomery, Jr., J. E. Peralta, F., Ogliaro, M., Bearpark, J. J. Heyd, E., Brothers, K. N. Kudin, V. N. Staroverov, R., Kobayashi, J., Normand, K., Raghavachari, A., Rendell, J. C. Burant, S. S. Iyengar, J., Tomasi, M., Cossi, N., Rega, J. M. Millam, M., Klene, J. E. Knox, J. B. Cross, V., Bakken, C., Adamo, J., Jaramillo, R., Gomperts, R. E. Stratmann, O., Yazyev, A. J. Austin, R., Cammi, C., Pomelli, J. W. Ochterski, R. L. Martin, K., Morokuma, V. G. Zakrzewski, G. A. Voth, P., Salvador, J. J. Dannenberg, S., Dapprich, A. D. Daniels, O., Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
24. S.-I. Kato, T. Matsumoto, M. Shigeiwa, H. Gorohmaru, S. Maeda, T. Ishi-i, and S. Mataka Novel 2,1,3-benzothiadiazole-based red-fluorescent dyes with enhanced two-photon absorption cross-sections Chem. Eur. J. 12 2006 2303 2307
25. Patent, WO01/49768.
26. J.-J. Kim, H. Choi, J.-W. Lee, M.-S. Kang, K. Song, S.O. Kang, and J. Ko A polymer gel electrolyte to achieve ≥6% power conversion efficiency with a novel organic dye incorporating a low-band-gap chromophore J. Mater. Chem. 18 2008 5223 5229
27. C.S. Li, Y.H. Tsai, W.C. Lee, and W.J. Kuo Synthesis and photophysical properties of pyrrole/polycyclic aromatic units hybrid fluorophores J. Org. Chem. 75 2010 4004 4013
28. K. Ohta, Y. Chiba, T. Ogawa, and Y. Endo Promising core structure for nuclear receptor ligands: design and synthesis of novel estrogen receptor ligands based on diphenylamine skeleton Bioorg. Med. Chem. Lett. 18 2008 5050 5053
29. H. Konno, S. Aimoto, S.O. Smith, K. Nosaka, and K. Akaji Synthesis of [19,35, 36-(13)C(3)]-labeled TAK779 as a molecular probe Bioorg. Med. Chem. 17 2009 5769 5774
30. A. Pron, G. Zhou, H. Norouzi-Arasi, M. Baumgarten, and K. Mullen Controlling the charge transfer in phenylene-bridged borylene-amine pi-conjugated systems Org. Lett. 11 2009 3550 3553
31. J. Svoboda, P. Stenclova, F. Uhlík, J. Zedník, and J. Vohlídal Synthesis and photophysical properties of α, (-bis(terpyridine)oligothiophenes Tetrahedron 67 2011 75 79
32. I.B. Berlman Empirical correlation between nuclear conformation and certain fluorescence and absorption characteristics of aromatic compounds J. Phys. Chem. 74 1970 3085 3093
33. N.I. Nijegorodov, and W.S. Downey The influence of planarity and rigidity on the absorption and fluorescence parameters and intersystem crossing rate constant in aromatic molecules J. Phys. Chem. 98 1994 5639 5643
34. H.L. Zhang, G. Zhao, Y. Ding, and B. Wu An efficient and enantioselective approach to the azaspirocyclic core of alkaloids: formal synthesis of halichlorine and pinnaic acid J. Org. Chem. 70 2005 4954 4961 (Pubitemid 40863895)
35. J.R. Lakowicz Principles of Fluorescence Spectroscopy 3rd edition 2006 Springer Science+Business Media NY, USA
36. F.B. Dias, S. Pollock, G. Hedley, L.O. Palsson, A. Monkman, I.I. Perepichka, I.F. Perepichka, M. Tavasli, and M.R. Bryce Intramolecular charge transfer assisted by conformational changes in the excited state of fluorene-dibenzothiophene-S,S-dioxide co-oligomers J. Phys. Chem. B 110 2006 19329 19339 (Pubitemid 44626408)
37. Z.R. Grabowski, K. Rotkiewicz, and W. Rettig Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem. Rev. 103 2003 3899 4032
38. J. Herbich, and A. Kapturkiewicz Electronic structure and molecular conformation in the excited charge transfer singlet states of 9-acridyl and other aryl derivatives of aromatic amines J. Am. Chem. Soc. 120 1998 1014 1029 (Pubitemid 28089898)