Two novel π-conjugated carbazole derivatives with blue two-photon-excited fluorescence

被引:17
作者
Hu, Zhang-Jun [1 ]
Sun, Ping-Ping [1 ]
Li, Lin [1 ]
Tian, Yu-Peng [1 ,2 ]
Yang, Jia-Xiang [1 ,2 ]
Wu, Jie-Ying [1 ]
Zhou, Hong-Ping [1 ]
Tao, Li-Ming [3 ]
Wang, Chuan-Kui [3 ]
Li, Ming [4 ]
Cheng, Guang-Hua [4 ]
Tang, Huo-Hong [5 ]
Tao, Xu-Tang [2 ]
Jiang, Min-Hua [2 ]
机构
[1] Anhui Univ, Dept Chem, Hefei 230039, Peoples R China
[2] Shandong Univ, State Key Lab Crystal Mat, Jinan 250100, Peoples R China
[3] Shandong Normal Univ, Dept Phys, Jinan 250014, Peoples R China
[4] Chinese Acad Sci, Xian Inst Opt & Precis Mech, State Key Lab Transient Opt & Photon, Xian 710119, Peoples R China
[5] Univ Sci & Technol China, Dept Precis Machinery & Precis Instrumentat, Anhua 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
Two-photon-excited fluorescence; Blue fluorescence; Carbazole; Alkylate; NONLINEAR-OPTICAL PROPERTIES; EXCITATION CROSS-SECTIONS; LIGHT-EMITTING-DIODES; ORGANIC-MOLECULES; FACILE SYNTHESIS; ONE-PHOTON; ABSORPTION; CHROMOPHORES; INITIATORS; DYES;
D O I
10.1016/j.chemphys.2008.10.031
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Two novel asymmetric D-pi-D' type chromophores with blue two-photon-excited fluorescences, (E)-3-(4-(methylthio)styryl)-9-etllyl-carbazole (T1) and (E)-3-(4-(methylthio)styryl)-9-hexyl-carbazole (T2), were synthesized via a solvent-free Wittig-Horner reaction. All of the compounds obtained were fully characterized by IR, MS and NMR spectroscopies. The structure of T1 was determined by single crystal X-ray diffraction analysis. A mechanism for the formation of the target molecules is also presented. Linear and nonlinear optical properties of T1 and 12 were investigated both experimentally and theoretically. The results show that the two asymmetric D-pi-D' type dyes exhibit clear two-photon activities with efficient blue emissions. Finally, pilot studies based on nonlinear optical applications of the synthesized chromophores were also carried out. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:91 / 98
页数:8
相关论文
共 56 条
[41]   Structure-property relationships for two-photon absorbing chromophores:: Bis-donor diphenylpolyene and bis(styryl)benzene derivatives [J].
Rumi, M ;
Ehrlich, JE ;
Heikal, AA ;
Perry, JW ;
Barlow, S ;
Hu, ZY ;
McCord-Maughon, D ;
Parker, TC ;
Röckel, H ;
Thayumanavan, S ;
Marder, SR ;
Beljonne, D ;
Brédas, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9500-9510
[42]   Ultrabright supramolecular beacons based on the self-assembly of two-photon chromophores on metal nanoparticles [J].
Stellacci, F ;
Bauer, CA ;
Meyer-Friedrichsen, T ;
Wenseleers, W ;
Marder, SR ;
Perry, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (02) :328-329
[43]   Investigations and facile synthesis of a series of novel multi-functional two-photon absorption materials [J].
Tian, Yu-Peng ;
Li, Lin ;
Zhang, Ju-Zhou ;
Yang, Jia-Xiang ;
Zhou, Hong-Ping ;
Wu, Jie-Ying ;
Sun, Ping-Ping ;
Tao, Li-Min ;
Guo, Ya-Hui ;
Wang, Chuan-Kui ;
Xing, Hui ;
Huang, Wen-Hao ;
Tao, Xu-Tang ;
Jiang, Min-Hua .
JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (34) :3646-3654
[44]   The chemistry of dimethyl carbonate [J].
Tundo, P ;
Selva, M .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :706-716
[45]   Five orders-of-magnitude enhancement of two-photon absorption for dyes on silver nanoparticle fractal clusters [J].
Wenseleers, W ;
Stellacci, F ;
Meyer-Friedrichsen, T ;
Mangel, T ;
Bauer, CA ;
Pond, SJK ;
Marder, SR ;
Perry, JW .
JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (27) :6853-6863
[46]  
Woo HS, 2005, J KOREAN PHYS SOC, V46, P981
[47]   Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm [J].
Xu, C ;
Webb, WW .
JOURNAL OF THE OPTICAL SOCIETY OF AMERICA B-OPTICAL PHYSICS, 1996, 13 (03) :481-491
[48]   A facile synthesis and properties of multicarbazole molecules containing multiple vinylene bridges [J].
Yang, JX ;
Tao, XT ;
Yuan, CX ;
Yan, YX ;
Wang, L ;
Liu, Z ;
Ren, Y ;
Jiang, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3278-3279
[49]   Synthesis, structure and nonlinear optical properties of two new one and two-branch two-photon polymerization initiators [J].
Zhang, Xian ;
Yu, XiaoQiang ;
Sun, YuMing ;
Xu, HongYan ;
Feng, YunGuo ;
Huang, BoBiao ;
Tao, XuTang ;
Jiang, MinHua .
CHEMICAL PHYSICS, 2006, 328 (1-3) :103-110
[50]   Synthesis and nonlinear optical properties of two new two-photon initiators: Triphenylarnine derivatives [J].
Zhang, Xian ;
Yu, Xiaoqiang ;
Sun, Yuming ;
He, Wei ;
Wu, Yonghong ;
Feng, Yunguo ;
Tao, Xutang ;
Jiang, Minhua .
OPTICAL MATERIALS, 2006, 28 (12) :1366-1371