Aggregation-induced emission enhancement compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties

被引：176

作者：

Li, Haiyin

Chi, Zhenguo ^{[1
]}

Xu, Bingjia

Zhang, Xiqi

Li, Xiaofang

Liu, Siwei

Zhang, Yi

Xu, Jiarui

机构：

[1] Sun Yat Sen Univ, PCFM Lab, Sch Chem & Chem Engn, OFCM Inst,State Key Lab Optoelect Mat & Technol, Guangzhou 510275, Guangdong, Peoples R China

来源：

JOURNAL OF MATERIALS CHEMISTRY | 2011年 / 21卷 / 11期

基金：

中国国家自然科学基金;

关键词：

RESTRICTED INTRAMOLECULAR ROTATION; ORGANIC NANOPARTICLES; LUMINESCENCE; FLUOROPHORES; ASSEMBLIES;

D O I：

10.1039/c0jm02571b

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：

New compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties are synthesized by the Wittig-Horner reaction. The compounds exhibit weak emission in good solvents, but strong fluorescence in aggregates or in the solid state, indicating that they are aggregation-induced emission enhancement compounds. The symmetry of their molecular structure affects their aggregation structures and photoluminescence emission properties in aggregation. These compounds show high thermal stabilities with glass transition temperatures between 168-177 degrees C and decomposition temperatures between 521-537 degrees C. The HOMO levels of the compounds are in the region of 4.92-4.94 eV, very close to the work function of indium tin oxide anode (4.8-5.0 eV). One of the compounds exhibits obvious piezofluorochromic behavior. The piezofluorochromic nature is generated through changing the mode of molecular packing under external pressure.

引用

页码：3760 / 3767

页数：8

共 28 条

[1] Enhanced emission and its switching in fluorescent organic nanoparticles [J].

An, BK ;

Kwon, SK ;

Jung, SD ;

Park, SY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14410-14415

[2] 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

[3] 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

[4] 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

[5] 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

[6] Effect of the amino group on the properties of 1-(benzylideneamino)pyridinium salts [J].

Gawinecki, R ;

Dobosz, R ;

Zakrzewska, A .

DYES AND PIGMENTS, 2004, 60 (02) :143-145

[7] Aggregation-induced emission: phenomenon, mechanism and applications [J].

Hong, Yuning ;

Lam, Jacky W. Y. ;

Tang, Ben Zhong .

CHEMICAL COMMUNICATIONS, 2009, (29) :4332-4353

[8] 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

[9] Multibranched triarylamine end-capped triazines with aggregation-induced emission and large two-photon absorption cross-sections [J].

Jiang, Yihua ;

Wang, Yaochuan ;

Hua, Jianli ;

Tang, Jin ;

Li, Bo ;

Qian, Shixiong ;

Tian, He .

CHEMICAL COMMUNICATIONS, 2010, 46 (26) :4689-4691

[10] Oligo(p-phenylene vinylene)s as a "New" class of piezochromic fluorophores [J].

Kunzelman, Jill ;

Kinami, Maki ;

Crenshaw, Brent R. ;

Protasiewicz, John D. ;

Weder, Christoph .

ADVANCED MATERIALS, 2008, 20 (01) :119-122

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