The synthesis, two-photon absorption and blue upconversion fluorescence of novel, nitrogen-containing heterocyclic chromophores

被引：36
作者：
Sun, Yi-Feng [1 ,2 ]
Huang, Wei [1 ]
Lu, Chang-Gui [1 ]
Cui, Yi-Ping [1 ]
机构：
[1] Southeast Univ, Sch Elect Sci & Engn, Adv Photon Ctr, Nanjing 210096, Peoples R China
[2] Taishan Univ, Dept Chem, Tai An 271021, Shandong, Peoples R China
来源：
DYES AND PIGMENTS | 2009年 / 81卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Two-photon absorption; Nonlinear transmission; Heterocycle; 1,2,4-Triazine; Imidazole; Crystal structure; OPTICAL-PROPERTIES; DERIVATIVES;
D O I：
10.1016/j.dyepig.2008.08.003
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Novel, nitrogen-containing heterocyclic chromophores based on either 1,2,4-triazine or an imidazole core were synthesized using a three-component, one-pot reaction under microwave irradiation. Structures were verified by H-1 NMR, IR, MS and elemental analyses while crystal structure was determined using X-ray diffraction. The two-photon absorption and two-photon upconverted blue fluorescent emission characteristics were investigated experimentally: preliminary structure-photophysical property relationships were established. Chromophores that contained the imidazole moiety displayed more potent two-photon absorption than compounds based upon 1,2,4-triazine and also exhibited a strong two-photon upconverted blue fluorescent emission peak at around 443-476 nm. Significant enhancement of the two-photon absorption cross-section was achieved by fusing a benzoxazole moiety onto the phenanthro[9,10-d]imidazole ring. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10 / 17
页数：8
相关论文
共 35 条
[1]   Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles [J].
Bellina, Fabio ;
Cauteruccio, Silvia ;
Rossi, Renzo .
TETRAHEDRON, 2007, 63 (22) :4571-4624
[2]   Two-photon 3D optical data storage via fluorescence modulation of an efficient fluorene dye by a photochromic diarylethene [J].
Corredor, Claudia C. ;
Huang, Zhen-Li ;
Belfield, Kevin D. .
ADVANCED MATERIALS, 2006, 18 (21) :2910-+
[3]   Synthesis, structure, and intense second harmonic generation of Λ-shaped s-triazine derivative [J].
Cui, YZ ;
Fang, Q ;
Huang, ZL ;
Xue, G ;
Yu, WT ;
Lei, H .
OPTICAL MATERIALS, 2005, 27 (10) :1571-1575
[4]   5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine [J].
Eltayeb, Naser Eltaher ;
Teoh, Siang Guan ;
Ng, Shea-Lin ;
Fun, Hoong-Kun ;
Ibrahim, Kamarulazizi .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O1041-O1042
[5]   3-(Benzoxazol-2-yl)-7-hydroxychromen-2-one methanol solvate [J].
Franca, EDF ;
Machado, AEH ;
Oliveira-Campos, AMF ;
Santos, S ;
Ellena, J ;
Guilardi, S .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2003, 59 :O820-O822
[6]   Structures and photophysics of lophine and double lophine derivatives [J].
Fridman, Natalya ;
Kaftory, Menahem ;
Speiser, Shammai .
SENSORS AND ACTUATORS B-CHEMICAL, 2007, 126 (01) :107-115
[7]   Synthesis and two-photon properties of new perylene bisimide derivatives [J].
Gao, Bo ;
Lu, Changgui ;
Xu, Jin ;
Meng, Fanshun ;
Cui, Yiping ;
Tian, He .
CHEMISTRY LETTERS, 2006, 35 (12) :1416-1417
[8]   2-PHOTON ABSORPTION AND OPTICAL-LIMITING PROPERTIES OF NOVEL ORGANIC-COMPOUNDS [J].
HE, GS ;
XU, GC ;
PRASAD, PN ;
REINHARDT, BA ;
BHATT, JC ;
DILLARD, AG .
OPTICS LETTERS, 1995, 20 (05) :435-437
[9]   Synthesis and optical properties of two 2,2′: 6′,2"-Terpyridyl-based two-photon initiators [J].
Hu, Zhang-Jun ;
Yang, Jia-Xiang ;
Tian, Yu-Peng ;
Zhou, Hong-Ping ;
Tao, Xu-Tang ;
Xu, Gui-Bao ;
Yu, Wen-Tao ;
Yu, Xiao-Qiang ;
Jiang, Min-Hua .
JOURNAL OF MOLECULAR STRUCTURE, 2007, 839 (1-3) :50-57
[10]   Two-photon absorption of new multibranched chromophores based on bis(diphenylamino)stilbene [J].
Huang, Zezhu ;
Wang, Xiaomei ;
Li, Bo ;
Lv, Changgui ;
Xu, Jun ;
Jiang, Wanli ;
Tao, Xutang ;
Qian, Shixiong ;
Chui, Yiping ;
Yang, Ping .
OPTICAL MATERIALS, 2007, 29 (08) :1084-1090
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