Synthesis, photophysical properties and TD-DFT calculation of four two-photon absorbing triphenylamine derivatives

Science China Chemistry

Volumn 56, Issue 1, 2013, Pages 106-116

  Kong, Lin ^a   Yang, Jiaxiang ^a,b   Zhou, Hongping ^a   Li, Shengli ^a   Hao, Fuying ^a   Zhang, Qiong ^a   Tu, Yulong ^a   Wu, Jieying ^a   Xue, Zhaoming ^a   Tian, Yupeng ^a,b,c  

^a ANHUI UNIVERSITY   (China)

^b SHANDONG UNIVERSITY   (China)

^c NANJING UNIVERSITY   (China)

Author keywords

optical properties; structure property relationship; TD DFT calculation; triphenylamine derivatives

Indexed keywords

CONJUGATED LENGTH; EXCITED FLUORESCENCE; FLUORESCENCE LIFETIMES; FLUORESCENCE QUANTUM YIELD; GAIN INSIGHT; LINEAR ABSORPTION; NON-LINEAR OPTICAL PROPERTIES; PHOTOPHYSICAL PROPERTIES; SOLVENT POLARITY; STRUCTURE PROPERTY RELATIONSHIPS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRIPHENYLAMINE DERIVATIVES; TWO PHOTON; TWO-PHOTON EXCITED FLUORESCENCE;

FLUORESCENCE; OPTICAL PROPERTIES; ORGANIC POLYMERS; PHOTONS; QUANTUM YIELD; SOLVENTS;

DENSITY FUNCTIONAL THEORY;

EID: 84872615654     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-012-4794-4     Document Type: Conference Paper

References (29)

1. Zhang XJ, Zhang XH, Zou K, Lee CS, Lee ST. Single-crystal nanoribbons, nanotubes, and nanowires from intramolecular charge-transfer organic molecules. J Am Chem Soc, 2007, 129: 3527-3532
2. Wang HZ, Zheng XG, Mao WD, Yu ZX, Gao ZL, Yang GQ, Wang PF, Wu SK. Efficient up-conversion fluorescence in charge transfer compound crystal. Appl Phys Lett, 1995, 66: 2777-2779
3. Nepraš M, Almonasy N, Bureš F, Kulhánek J, Dvořák M, Michl M. Fluorescence and photophysical properties of D-π-A push-pull systems featuring a 4, 5-dicyanoimidazole unit. Dyes Pigments, 2011, 91: 466-473
4. Cremer J, Briehn CA. Novel highly fluorescent triphenylamine-based oligothiophenes. Chem Mater, 2007, 19: 4155-4165
5. Mitschke U, Bäuerle P. The electroluminescence of organic materials. J Mater Chem, 2000, 10: 1471-1507
6. Dimitrakopoulos CD, Malenfant P. Organic thin film transistors for large area electronics. Adv Mater, 2002, 14: 99-117
7. Xu W, Peng B, Chen J, Liang M, Cai FS. New triphenylamine-based dyes for dye-sensitized solar cells. J Phys Chem C, 2008, 112: 874-880
8. Satoh N, Nakashima T, Yamamoto K. Metal-assembling dendrimers with a triarylamine core and their application to a dye-sensitized solar cell. J Am Chem Soc, 2005, 127: 13030-13038
9. Wang Q, Zakeeruddin SM, Cremer J, Bäuerle P, Humphry-Baker R, Grätzel M. Cross surface ambipolar charge percolation in molecular triads on mesoscopic oxide films. J Am Chem Soc, 2005, 127: 5706-6713
10. Bonhôte P, Moser JE, Humphry-Baker R, Vlachopoulos N, Zakeeruddin SM, Walder L, Grätzel M. Long-lived photoinduced charge separation and redox-type photochromism on mesoporous oxide films sensitized by molecular dyads. J Am Chem Soc, 1999, 121: 1324-1336
11. Tian YP, Li L, Zhang JZ, Yang JX, Zhou HP, Wu JY, Sun PP, Tao LM, Guo YH, Wang CK, Xing H, Huang WH, Tao XT, Jiang MH. Investigations and facile synthesis of a series of novel multifunctional two-photon absorption materials. J Mater Chem, 2007, 17: 3646-3654
12. He Z, Kan CW, Ho CL, Wong WY, Chui CH, Tong KL, So SK, Lee TH, Leung LM, Lin ZY. Light-emitting dyes derived from bifunctional chromophores of diarylamine and oxadiazole: Synthesis, crystal structure, photophysics and electroluminescence. Dyes Pigments, 2011, 88: 333-343
13. Chen XH, Zhao Z, Liu Y, Lu P, Wang YG. Synthesis and properties of 1-(4-aminophenyl)-2, 4-dicyano-3-diethylamino-9,9-diethylfluorenes: potential fluorescent material. Chem Lett, 2008, 37: 570-571
14. Li XC, Lim WT, Kim SH, Son YA. Crystal structure of 2-(4-(diphenylamino)- benzylidene)malononitrile, C22H15N3. New Cryst Struc, 2009, 224: 493-494
15. Lin YD, Peng YS, Su W, Tu CH, Sun CH, Chow TJ. A highly selective colorimetric and turn-on fluorescent probe for cyanide anion. Tetrahedron, 2012, 68: 2523-2526
16. Liu B, Zhang Q, Ding HJ, Hu GJ, Du YJ, Wang CK, Wu JY, Li SL, Zhou HP, Yang JX, Tian YP. Synthesis, crystal structures and two-photon absorption properties of a series of terpyridine-based chromophores. Dyes Pigments, 2012, 95: 149-160
17. Mimaite V, Grazulevicius JV, Ostrauskaite J, Jankauskas V. Synthesis and properties of triphenylamine-based hydrazones with reactive vinyl groups. Dyes Pigments, 2012, 95: 47-52
18. Zhou HP, Zhou FX, Wu P, Zheng Z, Yu ZP, Chen YX, Tu YL, Kong L, Wu JY, Tian YP. Three new five-coordinated mercury (II) dyes: Structure and enhanced two-photon absorption. Dyes Pigments, 2011, 91: 237-247
19. Wu SK. The Problem on photophysics and photochemistry of organic compounds possessing ability of fluorescence emission. Prog Chem, 2005, 17: 15-39
20. Berezin MY, Achilefu S. Fluorescence lifetime measurements and biological imaging. Chem Rev, 2010, 110: 2641-2684
21. Förster T, Kasper K. Ein konzentrationsumschlag der fluoreszenz. Z Phys Chem N F, 1954, 1: 275-277
22. Förster T. Excimere. Angew Chem Int Ed Engl, 1969, 8: 333-343
23. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr. JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Wallingford, CT: Gaussian, Inc, 2004
24. Li DM, Zhang Q, Hossain AMS, Sun M, Wu JY, Yang JX, Zhou HP, Tao LM, Wang CK, Tian YP, Crystal structures, two-photon absorption and theoretical calculation of a series of bis-vinylpyridine compounds synthesized by one-step solid state reaction. Sci Chin Chem, 2010, 54: 730-736
25. Yang JX, Wang CX, Li L, Lin N, Tao XT, Tian YP, Zhao X, Jiang MH. Investigation of structure-property relationships of multibranched two-photon absorption chromophores based on π-conjugation core. Chem Phys, 2009, 358: 39-44
26. Xu C, Webb WW. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B, 1996, 13: 481-491
27. Ajami A, Husinsky W, Liska R, Pucher N. Two-photon absorption cross section measurements of various two-photon initiators for ultrashort laser radiation applying the Z-scan technique. J Opt Soc Am B, 2010, 27: 2290-2297
28. Jeong HC, Piao MJ, Lee SH, Jeong MY, Kang KM, Park G, Jeon SJ, Cho BR. Octupolar dendrimers with large first hyperpolarizability. Adv Func Mater, 2004, 14: 64-70
29. Varnavski O, Goodson T, Sukhomlinova L, Twieg R. Ultrafast exciton dynamics in a branched molecule investigated by time-resolved fluorescence, transient absorption, and three-pulse photon echo peak shift measurements. J Phys Chem B, 2004, 108: 10484-10492