Theoretical study of substituent effect on the charge mobility of 2,5-bis(trialkylsilylethynyl)-1,1,3,4-tetraphenylsiloles

Science China Chemistry

Volumn 53, Issue 11, 2010, Pages 2311-2317

  Zhao, Zujin ^a   Liu, Dandan ^b   Lam, Jacky Wing Yip ^a   Lu, Ping ^b   Yang, Bing ^b   Ma, Yuguang ^b   Tang, Ben Zhong ^a,c  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b Jilin University   (China)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

charge mobility; electronic structure; silole; substitution effect; theoretical calculation

Indexed keywords

CHARGE MOBILITIES; COUPLING MATRIX ELEMENT; HIGH ELECTRON MOBILITY; HOLE TRANSFER; REORGANIZATION ENERGIES; SILOLE; SUBSTITUENT EFFECT; SUBSTITUTION EFFECT; THEORETICAL CALCULATIONS; THEORETICAL STUDY; TRIMETHYL;

ELECTRON MOBILITY; ELECTRONIC STRUCTURE;

ELECTRONIC PROPERTIES;

EID: 78649370039     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4079-8     Document Type: Article

References (26)

1. V.N. Khabashesku V. Balaji S.E. Boganov O.M. Nefedov J. Michl 1994 Matrix isolation of silacyclopentadienes: UV-visible and IR spectra and photochemical interconversion J Am Chem Soc 116 320 329 1:CAS:528:DyaK2cXhtlClsL4%3D 10.1021/ja00080a037
2. Yamaguchi S, Tamao K. Silole-containing σ- and π-conjugated compounds. J Chem Soc Dalton Trans, 1998, 3693-3702
3. A.J. Mäkinen M. Uchida Z.H. Kafafi 2004 Electronic structure of a silole derivative-magnesium thin film interface J Appl Phys 95 2832 2838 10.1063/1.1643190
4. H. Murata Z.H. Kafafi M. Uchida 2002 Efficient organic light-emitting diodes with undoped active layers based on silole derivatives Appl Phys Lett 80 189 191 1:CAS:528:DC%2BD38XjsVChtA%3D%3D 10.1063/1.1432109
5. B.Z. Tang X. Zhan G. Yu P.P.S. Lee Y. Liu D. Zhu 2001 Efficient blue emission from siloles J Mater Chem 11 2974 2978 1:CAS:528:DC%2BD38XjsFCjtA%3D%3D 10.1039/b102221k
6. Z. Zhao S. Chen J.W.Y. Lam C.K.W. Jim C.Y.K. Chan Z. Wang P. Lu H.S. Kwok Y. Ma B.Z. Tang 2010 Steric hindrance, electronic communication, and energy transfer in the photo- and electroluminescence processes of aggregation-induced emission luminogens J Phys Chem C 114 7963 7972 1:CAS:528:DC%2BC3cXksF2msrc%3D 10.1021/jp910728x
7. H.Y. Chen J.W. Lam J.D. Luo Y.L. Ho B.Z. Tang D. Zhu M. Wong H.S. Kwok 2002 Highly efficient organic light-emitting diodes with a silole-based compound Appl Phys Lett 81 574 576 1:CAS:528:DC%2BD38XlsVamsLc%3D 10.1063/1.1495542
8. H. Usta G. Lu A. Facchetti T.J. Marks 2006 Dithienosilole- and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors J Am Chem Soc 128 9034 9035 1:CAS:528:DC%2BD28Xmt12msbY%3D 10.1021/ja062908g
9. Y.Q. Dong J.W.Y. Lam A.J. Qin Z. Li J.Z. Liu J.Z. Sun Y.P. Dong B.Z. Tang 2007 Endowing hexaphenylsilole with chemical sensory and biological probing properties by attaching amino pendants to the silolyl core Chem Phys Lett 446 124 127 1:CAS:528:DC%2BD2sXhtVCgtb3J 10.1016/j.cplett.2007.08.030
10. L. Peng M. Wang G. Zhang D. Zhang D. Zhu 2009 A fluorescence turn-on detection of cyanide in aqueous solution based on the aggregation-induced emission Org Lett 11 1943 1946 1:CAS:528:DC%2BD1MXktVGltrY%3D 10.1021/ol900376r
11. Y. Yu Y. Hong C. Feng J. Liu J.W.Y. Lam M. Faisal K.M. Ng K.Q. Luo B.Z. Tang 2009 Synthesis of an AIE-active fluorogen and its application in cell imaging Sci Chin Ser B Chem 52 15 19 1:CAS:528:DC%2BD1MXlvFClug%3D%3D 10.1007/s11426-009-0008-0
12. Mi B, Dong Y, Li Z, Lam JWY, Häuler M, Sung HHY, Kwok HS, Dong Y, Williams ID, Liu Y, Luo Y, Shuai Z, Zhu D, Tang BZ. Making silole photovoltaically active by attaching carbazolyl donor groups to the silolyl acceptor core. Chem Commun, 2005, 3583-3585
13. S. Yamaguchi T. Endo M. Uchida T. Izumizawa K. Furukawa K. Tamao 2000 Toward new materials for organic electroluminescent devices: synthesis, structures, and properties of a series of 2,5-diaryl-3,4-diphenylsiloles Chem Eur J 6 1683 1692 1:CAS:528:DC%2BD3cXjtlOju7Y%3D 10.1002/(SICI)1521- 3765(20000502)6:9<1683::AID-CHEM1683>3.3.CO;2-D
14. Luo JD, Xie ZL, Lam JWY, Cheng L, Chen HY, Qiu CF, Kwok HS, Zhan XW, Liu YQ, Zhu DB, Tang BZ. Aggregation-induced emission of 1-methyl-1,2,3,4,5- pentaphenylsilole. Chem Commun, 2001, 1740-1741
15. Z. Zhao S. Chen X. Shen F. Mahtab Y. Yu P. Lu J.W.Y. Lam H.S. Kwok B.Z. Tang 2010 Aggregation-induced emission, self-assembly, and electroluminescence of 4,4′-bis(1,2,2-triphenylvinyl)biphenyl Chem Commun 46 686 688 1:CAS:528:DC%2BC3cXnt1OltQ%3D%3D 10.1039/b915271g
16. Hong Y, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009, 4332-4353
17. J. Liu J.W.Y. Lam B.Z. Tang 2009 Aggregation-induced emission of silole molecules and polymers: Fundamental and applications J Inorg Organomet Polym 19 249 285 1:CAS:528:DC%2BD1MXovFWks7s%3D 10.1007/s10904-009-9282-8
18. Z. Zhao S. Chen J.W.Y. Lam C.Y.K. Chan C.K.W. Jim Z. Wang C. Wang P. Lu H.S. Kwok Y. Ma B.Z. Tang 2010 Luminescent tetraphenylethene-substituted silanes Pure Appl Chem 82 863 870 1:CAS:528:DC%2BC3cXlslyisb0%3D 10.1351/PAC-CON-09-09- 15
19. Z. Li Y. Dong J.W.Y. Lam J. Sun A. Qin M. Häuler Y. Dong H.H.Y. Sung I.D. Williams H.S. Kwok B.Z. Tang 2009 Functionalized siloles: Versatile synthesis, aggregation-induced emission, and sensory and device applications Adv Funct Mater. 19 1 13
20. Z. Zhao S. Chen J.W.Y. Lam P. Lu Y. Zhong K. Wong H.S. Kwok B.Z. Tang 2010 Creation of highly efficient solid emitter by decorating pyrene core with AIE-active tetraphenylethene peripheries Chem Commun 46 2221 2223 1:CAS:528:DC%2BC3cXjt1Khs7o%3D 10.1039/b921451h
21. Z. Zhao Z. Wang P. Lu C.Y.K. Chan D. Liu J.W.Y. Lam H.H.Y. Sung I.D. Williams Y. Ma B.Z. Tang 2009 Structural modulation of solid-state emission of 2,5-bis(trialkylsilylethynyl)-3,4-diphenylsiloles Angew Chem Int Ed 48 7608 7611 1:CAS:528:DC%2BD1MXht1Sru73M 10.1002/anie.200903698
22. G. Yu S.W. Yin Y.Q. Liu J.S. Chen X.J. Xu X.B. Sun D.G. Ma X.W. Zhan Q. Peng Z.G. Shuai B.Z. Tang D.B. Zhu W.H. Fang Y. Luo 2005 Structures, electronic states, photoluminescence, and carrier transport properties of 1,1-disubstituted 2,3,4,5-tetraphenylsiloles J Am Chem Soc 127 6335 6346 1:CAS:528: DC%2BD2MXjtFSjtLg%3D 10.1021/ja044628b
23. C. Risko G. P. Kushto Z. H. Kafafi J. L. Brédas 2004 Electronic properties of silole-based organic semiconductors J Chem Phys 121 9031 9038 1:CAS:528:DC%2BD2cXptFGltrg%3D 10.1063/1.1804155
24. X. Zhan C. Risko A. Korlyukov F. Sena T.V. Timofeeva M.Y. Antipin S. Barlow J.L. Brédas S.R. Marder 2006 Comparative studies of the geometric and electronic properties of 1,1-disubstituted-2,3,4,5-tetraphenylsiloles and 1,1,2,2-tetramethyl-3,4,5,6-tetraphenyl-1,2-disila-3,5-cyclohexadiene J Mater Chem 16 3814 3822 1:CAS:528:DC%2BD28XhtValtbrN 10.1039/b605343b
25. Marcus R A. Electron transfer reactions in chemistry. Theory and experiment. Rev Mod Phys, 993, 65: 599-610
26. R.A. Marcus H. Eyring 1964 Chemical and electrochemical electron-transfer theory Annu Rev Phys Chem 15 155 196 1:CAS:528:DyaF2cXkslaksro%3D 10.1146/annurev.pc.15.100164.001103