Synthesis and Characterization of Triphenylethylene Derivatives with Aggregation-Induced Emission Characteristics

被引:55
作者
Li, Xiao-Fang [1 ]
Chi, Zhen-Guo [1 ]
Xu, Bing-Jia [1 ]
Li, Hai-Yin [1 ]
Zhang, Xi-Qi [1 ]
Zhou, Wei [1 ]
Zhang, Yi [1 ]
Liu, Si-Wei [1 ]
Xu, Jia-Rui [1 ]
机构
[1] Sun Yat Sen Univ, State Key Lab Optoelect Mat & Technol, DSAPM Lab,FCM Inst,Sch Chem & Chem Engn, PCFM Lab,KLGHEI Environm & Energy Chem, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
Triphenylethylene; Blue light emission; Thermal property stability; Synthesis; Aggregation-induced emission; ORGANIC NANOPARTICLES; TRIARYLAMINE;
D O I
10.1007/s10895-011-0896-1
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
New aggregation-induced emission (AIE) compounds derived from triphenylethylene were synthesized. The thermal, photophysical, electrochemical and aggregation-induced emissive properties were investigated. All the compounds had strong blue light emission capability and good thermal stability. Their maximum fluorescence emission wavelengths were between 443 to 461 nm in solid states, while their glass transition temperatures ranged from 86 to 129 degrees C. The decomposition temperatures of the synthesized compounds were in the range of 432-534 degrees C. The synthesized compounds possessed aggregation-induced emission properties, namely exhibited enhanced fluorescence emission in aggregated states. The highest occupied molecular orbital (HOMO) energy levels estimated from the oxidation potentials were between 5.61 and 5.66 eV and the lowest unoccupied molecular orbital/highest occupied molecular orbital (LUMO/HOMO) energy gap values were found to be in the range of 3.18-3.22 eV. The compounds 4-(4-(2,2-bis(4-(naphthalen-1-yl)phenyl)vinyl)phenyl) dibenzothiophene [(BN)(2)Bt] and 4-(4-(2,2-di(biphenyl-4-yl)vinyl)phenyl) dibenzothiophene [(BB)(2)Bt] exhibited vibronic fine-structure photoluminescence spectra when the water fraction was less than 70%.
引用
收藏
页码:1969 / 1977
页数:9
相关论文
共 23 条
[1]   Strongly fluorescent organogel system comprising fibrillar self-assembly of a trifluoromethyl-based cyanostilbene derivative [J].
An, BK ;
Lee, DS ;
Lee, JS ;
Park, YS ;
Song, HS ;
Park, SY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10232-10233
[2]   Relaxation dynamics and structural characterization of organic nanoparticles with enhanced emission [J].
Bhongale, CJ ;
Chang, CW ;
Lee, CS ;
Diau, EWG ;
Hsu, CS .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (28) :13472-13482
[3]   Aggregation-induced emission of cis,cis-1,2,3,4-tetraphenylbutadiene from restricted intramolecular rotation [J].
Chen, JW ;
Xu, B ;
Ouyang, XY ;
Tang, BZ ;
Cao, Y .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (37) :7522-7526
[4]   Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles [J].
Chen, JW ;
Law, CCW ;
Lam, JWY ;
Dong, YP ;
Lo, SMF ;
Williams, ID ;
Zhu, DB ;
Tang, BZ .
CHEMISTRY OF MATERIALS, 2003, 15 (07) :1535-1546
[5]   Aggregation-induced emission: phenomenon, mechanism and applications [J].
Hong, Yuning ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL COMMUNICATIONS, 2009, (29) :4332-4353
[6]   Triarylethene-based extended π-systems:: Programmable synthesis and photophysical properties [J].
Itami, K ;
Ohashi, Y ;
Yoshida, J .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2778-2792
[7]   New aggregation-induced emission enhancement materials combined triarylamine and dicarbazolyl triphenylethylene moieties [J].
Li, Haiyin ;
Chi, Zhenguo ;
Xu, Bingjia ;
Zhang, Xiqi ;
Yang, Zhiyong ;
Li, Xiaofang ;
Liu, Siwei ;
Zhang, Yi ;
Xu, Jiarui .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (29) :6103-6110
[8]   Aggregation-induced emission enhancement compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties [J].
Li, Haiyin ;
Chi, Zhenguo ;
Xu, Bingjia ;
Zhang, Xiqi ;
Li, Xiaofang ;
Liu, Siwei ;
Zhang, Yi ;
Xu, Jiarui .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (11) :3760-3767
[9]   Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J].
Luo, JD ;
Xie, ZL ;
Lam, JWY ;
Cheng, L ;
Chen, HY ;
Qiu, CF ;
Kwok, HS ;
Zhan, XW ;
Liu, YQ ;
Zhu, DB ;
Tang, BZ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1740-1741
[10]   FLUORESCENCE QUANTUM YIELD DETERMINATIONS - 9,10-DIPHENYLANTHRACENE AS A REFERENCE-STANDARD IN DIFFERENT SOLVENTS [J].
MORRIS, JV ;
MAHANEY, MA ;
HUBER, JR .
JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (09) :969-974