Amino substituted 4-pyridylbutadienes: Synthesis and fluorescence investigations

被引:9
作者
Agnihotri, Harsha [2 ]
Mahalingavelar, Paramasivam [2 ]
Mande, Hemant [1 ]
Ghalsasi, Prasanna [1 ]
Kanvah, Sriram [2 ]
机构
[1] Maharaja Sayajirao Univ Baroda, Dept Chem, Vadodara 390002, Gujarat, India
[2] Indian Inst Technol Gandhinagar, Dept Chem, Ahmadabad 382424, Gujarat, India
关键词
Solvatochromism; Pyridyl dyes; Donor-acceptor systems; Julolidine; Intramolecular charge transfer; Diarylpolyenes; INTRAMOLECULAR CHARGE-TRANSFER; EXCITED-STATE PROPERTIES; OPTICAL-PROPERTIES; MOLECULAR ROTORS; PYRIDINE RING; PHOTOISOMERIZATION; DERIVATIVES; DYES; PHOTOCHEMISTRY; PHOTOPHYSICS;
D O I
10.1016/j.dyepig.2015.08.018
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Synthesis and spectroscopic investigations of a series of donor-pi-acceptor systems containing pyridine as the electron withdrawing group and an amino derivative (dimethylamino, diphenylamino, carbazole and julolidine) as electron donating group, separated by a pi-spacer are described. The effect of varying donors on absorption and emission properties was studied in different solvents. All the molecules investigated exhibit pronounced positive polarity dependent solvatochromic shifts of up to similar to 141 nm. Strong fluorescence quantum yields are also observed for dienes containing carbazole and diphenylamine donors. This behavior suggests the presence of highly polar emitting states as a result of pi -pi* intramolecular charge-transfer (ICT). The observations were corroborated by a linear relation of the fluorescence maximum (nu(max)) versus the solvent polarity function (Delta(f)) from the Lippert-Mataga correlation. The emission lifetime shows a decay profile consistent with the formation of one species (1 and 3) and two species (2 and 4) in the excited state. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:341 / 348
页数:8
相关论文
共 48 条
[1]  
Amaral E, 2011, METHODS MOL BIOL, V689, P137, DOI 10.1007/978-1-60761-950-5_8
[2]   Functional π-Gelators and Their Applications [J].
Babu, Sukumaran Santhosh ;
Praveen, Vakayil K. ;
Ajayaghosh, Ayyappanpillai .
CHEMICAL REVIEWS, 2014, 114 (04) :1973-2129
[3]   Rotamerism and electronic spectra of aza-derivatives of stilbene and diphenylbutadiene. A combined experimental and theoretical study [J].
Baraldi, I ;
Spalletti, A ;
Vanossi, D .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2003, 59 (01) :75-86
[4]   Photoisomerization mechanisms and photoselectivity of the stereoisomers of 1-(pyrid-n-yl),4-phenylbuta-1,3-diene [J].
Bartocci, G ;
Galiazzo, G ;
Latterini, L ;
Marri, E ;
Mazzucato, U ;
Spalletti, A .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2002, 4 (13) :2911-2916
[5]   Photophysics and photochemistry of the EE and ZE isomers of 1-(n-pyridyl)-4-phenyl-1,3-butadiene (n=2, 3 and 4) [J].
Bartocci, G ;
Galiazzo, G ;
Mazzucato, U ;
Spalletti, A .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (03) :379-386
[6]   Effect of the nature of aryl and heteroaryl groups on the excited state properties of asymmetric 1,4-diarylbutadienes [J].
Bartocci, G ;
Galiazzo, G ;
Gennari, G ;
Marri, E ;
Mazzucato, U ;
Spalletti, A .
CHEMICAL PHYSICS, 2001, 272 (2-3) :213-225
[7]   π-Conjugated Zwitterions as Paradigm of Donor-Acceptor Building Blocks in Organic-Based Materials [J].
Beverina, Luca ;
Pagani, Giorgio A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :319-329
[8]   Fluorescent neuroactive probes based on stilbazolium dyes [J].
Brown, Adrienne S. ;
Bernal, Lisa-Marie ;
Micotto, Teresa L. ;
Smith, Erika L. ;
Wilson, James N. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2142-2148
[9]   Quadratic optical nonlinearities of N-methyl and N-aryl pyridinium salts [J].
Coe, BJ ;
Harris, JA ;
Asselberghs, I ;
Wostyn, K ;
Clays, K ;
Persoons, A ;
Brunschwig, BS ;
Coles, SJ ;
Gelbrich, T ;
Light, ME ;
Hursthouse, MB ;
Nakatani, K .
ADVANCED FUNCTIONAL MATERIALS, 2003, 13 (05) :347-357
[10]   Organic Sensitizers with Pyridine Ring Anchoring Group for p-Type Dye-Sensitized Solar Cells [J].
Cui, Jin ;
Lu, Jianfeng ;
Xu, Xiaobao ;
Cao, Kun ;
Wang, Zhong ;
Alemu, Getachew ;
Yuang, Huailiang ;
Shen, Yan ;
Xu, Jie ;
Cheng, Yibing ;
Wang, Mingkui .
JOURNAL OF PHYSICAL CHEMISTRY C, 2014, 118 (30) :16433-16440