Twisted Intramolecular Charge Transfer and Aggregation-Induced Emission of BODIPY Derivatives

被引：915

作者：

Hu, Rongrong ^{[2
]}

Lager, Erik ^{[1
]}

Aguilar-Aguilar, Angelica ^{[1
]}

Liu, Jianzhao ^{[2
]}

Lam, Jacky W. Y. ^{[2
]}

Sung, Herman H. Y. ^{[2
]}

Williams, Ian D. ^{[2
]}

Zhong, Yongchun ^{[3
]}

Wong, Kam Sing ^{[3
]}

Pena-Cabrera, Eduardo ^{[1
]}

Tang, Ben Zhong ^{[2
,4
]}

机构：

[1] Univ Guanajuato, Dept Quim, Guanajuato 36050, Gto, Mexico

[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

[3] Hong Kong Univ Sci & Technol, Dept Phys, Kowloon, Hong Kong, Peoples R China

[4] Zhejiang Univ, Dept Polymer Sci & Engn, Inst Biomed Macromol, Minist Educ,Key Lab Macromol Synth & Functionaliz, Hangzhou 310003, Zhejiang, Peoples R China

来源：

JOURNAL OF PHYSICAL CHEMISTRY C | 2009年 / 113卷 / 36期

关键词：

TURN-ON DETECTION; HIGHLY FLUORESCENT; DUAL FLUORESCENCE; METAL-FREE; DYES; PHOTOLUMINESCENCE; STATE; POLYMERS; MOLECULES; VISCOSITY;

D O I：

10.1021/jp902962h

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：

Boron dipyrromethene (BODIPY) derivatives 1 and 2 consisting of donor and acceptor units with dual photoresponses to solvent polarity and luminogen aggregation are developed through taking advantage of twisted intramolecular charge transfer (TICT) and aggregation-induced emission (ATE) processes. In nonpolar solvents, the locally excited (LE) states of the BODIPY luminogens emit intense green lights. Increasing solvent polarity brings the luminogens from the LE state to the TICT state, causing a large bathochromic shift in the emission color but a dramatic decrease in the emission efficiency. The red emission is greatly boosted by aggregate formation or ATE effect: addition of large amounts of water into the solutions of 1 and 2 in the polar solvents causes the luminogens to aggregate supramolecularly and to emit efficiently. The emission can be enhanced by increasing solvent viscosity and decreasing solution temperature, indicating that the ATE effect is caused by the restriction of the intramolecular rotations in the aggregates of the luminogens.

引用

页码：15845 / 15853

页数：9

共 59 条

[21] PHOTOPHYSICS OF INTERNAL TWISTING [J].

LIPPERT, E ;

RETTIG, W ;

BONACICKOUTECKY, V ;

HEISEL, F ;

MIEHE, JA .

ADVANCES IN CHEMICAL PHYSICS, 1987, 68 :1-173

[22]

Lippert E., 1961, Angew. Chem, V73, P695, DOI DOI 10.1002/ANGE.19610732103

[23] Aggregation-induced Emission of Silole Molecules and Polymers: Fundamental and Applications [J].

Liu, Jianzhao ;

Lam, Jacky W. Y. ;

Tang, Ben Zhong .

JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2009, 19 (03) :249-285

[24]

Lopez A.F., 2005, Int. Rev. Phys. Chem, V24, P339

[25] BODIPY dyes and their derivatives: Syntheses and spectroscopic properties [J].

Loudet, Aurore ;

Burgess, Kevin .

CHEMICAL REVIEWS, 2007, 107 (11) :4891-4932

[26]

LUIS S, 1995, J AM CHEM SOC, V117, P3189

[27] 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

[28] Organization of acenes with a cruciform assembly motif [J].

Miao, Q ;

Chi, XL ;

Xiao, SX ;

Zeis, R ;

Lefenfeld, M ;

Siegrist, T ;

Steigerwald, ML ;

Nuckolls, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1340-1345

[29] Synthesis, crystal structure, and transistor performance of tetracene derivatives [J].

Moon, H ;

Zeis, R ;

Borkent, EJ ;

Besnard, C ;

Lovinger, AJ ;

Siegrist, T ;

Kloc, C ;

Bao, ZN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15322-15323

[30] Solid-State Emissive BODIPY Dyes with Bulky Substituents As Spacers [J].

Ozdemir, Tugba ;

Atilgan, Serdar ;

Kutuk, Ilker ;

Yildirim, Leyla T. ;

Tulek, Abdullah ;

Bayindir, Mehmet ;

Akkaya, Engin U. .

ORGANIC LETTERS, 2009, 11 (10) :2105-2107

← 1 2 3 4 5 6 →