Modulation of the Photophysical Properties of β-substituted BODIPY Dyes

被引:10
作者
More, Ankush B. [1 ]
Chakraborty, Goutam [2 ]
Mula, Soumyaditya [3 ]
Ray, Alok K. [2 ]
Sekar, Nagaiyan [1 ]
机构
[1] Inst Chem Technol, Dept Dyestuff Technol, Bombay 400019, Maharashtra, India
[2] Bhabha Atom Res Ctr, Laser & Plasma Technol Div, Bombay 400085, Maharashtra, India
[3] Bhabha Atom Res Ctr, Div Bioorgan, Bombay 400085, Maharashtra, India
关键词
BODIPY; ICT; Radiative and nonradiative process and DFT; FUNCTIONALIZATION; FLUOROPHORES; DERIVATIVES; COMPLEXES;
D O I
10.1007/s10895-017-2200-5
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Photophysical properties of BODIPY dyes containing acetyl acetone and benzoyl acetone BF2 unit as an electron accepting substituent at beta position linked via double bond have been investigated using a wide range of solvents of different polarities. The substitution effect at beta position of the BODIPY dyes on their absorption, emission and quantum yield of fluorescence have been the aim of present study. For the synthesized BODIPY dyes fluorescence quantum yields and lifetimes show very sharp decrease with an increase in the solvent polarity, suggesting the involvement of highly polar ICT state de-excitation mechanism along with the local excitation process. The polarity dependent changes in average fluorescence life time and quantum yield values rationalize the formation of ICT states.
引用
收藏
页码:381 / 392
页数:12
相关论文
共 29 条
[1]   Calculation of excitation energies within time-dependent density functional theory using auxiliary basis set expansions [J].
Bauernschmitt, R ;
Haser, M ;
Treutler, O ;
Ahlrichs, R .
CHEMICAL PHYSICS LETTERS, 1997, 264 (06) :573-578
[2]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[3]   Fluorescent indicators based on BODIPY [J].
Boens, Noel ;
Leen, Volker ;
Dehaen, Wim .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172
[4]   Tetrastyryl-Bodipy Dyes: Convenient Synthesis and Characterization of Elusive Near IR Fluorophores [J].
Buyukcakir, Onur ;
Bozdemir, O. Altan ;
Kolemen, Safacan ;
Erbas, Sundus ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2009, 11 (20) :4644-4647
[5]   Boranil and Related NBO Dyes: Insights From Theory [J].
Chibani, Siwar ;
Charaf-Eddin, Azzam ;
Le Guennic, Boris ;
Jacquemin, Denis .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2013, 9 (07) :3127-3135
[6]   Distyryl-boradiazaindacenes: facile synthesis of novel near IR emitting fluorophores [J].
Dost, Zeynep ;
Atilgan, Serdar ;
Akkaya, Engin U. .
TETRAHEDRON, 2006, 62 (36) :8484-8488
[7]  
Frisch M.J., 2009, GAUSSIAN INC WALLING, V27, P34
[8]   AIE-active organoboron complexes with highly efficient solid-state luminescence and their application as gas sensitive materials [J].
Gong, Shuwen ;
Liu, Qingsong ;
Wang, Xiaoqing ;
Xia, Bo ;
Liu, Zhipeng ;
He, Weijiang .
DALTON TRANSACTIONS, 2015, 44 (31) :14063-14070
[9]   β-Formyl-BODIPYs from the Vilsmeier-Haack Reaction [J].
Jiao, Lijuan ;
Yu, Changjiang ;
Li, Jilong ;
Wang, Zhaoyun ;
Wu, Min ;
Hao, Erhong .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7525-7528
[10]   BODIPY dyes in photodynamic therapy [J].
Kamkaew, Anyanee ;
Lim, Siang Hui ;
Lee, Hong Boon ;
Kiew, Lik Voon ;
Chung, Lip Yong ;
Burgess, Kevin .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (01) :77-88