Photo- and solvatochromic properties of nitrobenzospiropyran in ionic liquids containing the [NTf2]- anion

被引:42
作者
Byrne, Robert [1 ]
Fraser, Kevin J. [2 ]
Izgorodina, Ekaterina [2 ]
MacFarlane, Douglas R. [2 ]
Forsyth, Maria [3 ]
Diamond, Dermot [1 ]
机构
[1] Dublin City Univ, Sch Chem Sci, Natl Ctr Sensor Res, Adapt Sensors Grp, Dublin 9, Ireland
[2] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
[3] Monash Univ, Sch Phys & Mat Engn, ARC Ctr Nanostructured Electromat, Clayton, Vic 3800, Australia
基金
爱尔兰科学基金会;
关键词
D O I
10.1039/b806641h
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
The photo-, thermo- and solvatochromic properties of 2,3-dihydro-1',3',3'-trimethyl-6-nitrospiro[1-benzopyran-2,2'-1H-indole] (BSP-NO2) were studied in ILs containing the anion [NTf2](-) by UV-Vis absorption spectroscopy, ab initio molecular orbital theory and density functional theory (DFT) calculations. It was found that the kinetics and thermodynamics of the BSP-NO2 <-> MC (merocyanine) equilibrium was sensitive to the nature of the cation. It was also observed that the imidazolium cation can form a through-space orbital interaction with the MC isomer, rather than a simple electrostatic interaction, thus preventing the MC conversion back to the BSP-NO2 isomer. The BSP-NO2 <-> MC equilibrium thus serves as a model system for studying modes of interaction of the cations in ionic liquids.
引用
收藏
页码:5919 / 5924
页数:6
相关论文
共 53 条
[1]  
[Anonymous], 2002, ACS S SER
[2]   Measurements of the complete solvation response in ionic liquids [J].
Arzhantsev, Sergei ;
Jin, Hui ;
Baker, Gary A. ;
Maroncelli, Mark .
JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (18) :4978-4989
[3]   Group 15 quaternary alkyl bistrflimides: ionic liquids with potential application in electropositive metal deposition and as supporting electrolytes [J].
Bhatt, AI ;
May, I ;
Volkovich, VA ;
Hetherington, ME ;
Lewin, B ;
Thied, RC ;
Ertok, N .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2002, (24) :4532-4534
[4]   COLOR AND CONSTITUTION .13. MEROCYANINES AS SOLVENT PROPERTY INDICATORS [J].
BROOKER, LGS ;
CRAIG, AC ;
HESELTINE, DW ;
JENKINS, PW ;
LINCOLN, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (11) :2443-+
[5]   THE EFFECT OF SOLVENTS UPON EQUILIBRIA, SPECTRA, AND REACTION RATES [J].
BROWNSTEIN, S .
CANADIAN JOURNAL OF CHEMISTRY, 1960, 38 (09) :1590-1596
[6]   Photo-regenerable surface with potential for optical sensing [J].
Byrne, RJ ;
Stitzel, SE ;
Diamond, D .
JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (14) :1332-1337
[7]   Chemo/bio-sensor networks [J].
Byrne, Robert ;
Diamond, Dermot .
NATURE MATERIALS, 2006, 5 (06) :421-424
[8]   Dynamics of photoisomerisation and rotational relaxation of 3,3′-diethyloxadicarbocyanine iodide in room temperature ionic liquid and binary mixture of ionic liquid and water [J].
Chakrabarty, D ;
Chakraborty, A ;
Hazra, P ;
Seth, D ;
Sarkar, N .
CHEMICAL PHYSICS LETTERS, 2004, 397 (1-3) :216-221
[9]   Ionic liquids: solvent properties and organic reactivity [J].
Chiappe, C ;
Pieraccini, D .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) :275-297
[10]   Photochromic compounds: Chemistry and application in ophthalmic lenses [J].
Crano, JC ;
Flood, T ;
Knowles, D ;
Kumar, A ;
VanGemert, B .
PURE AND APPLIED CHEMISTRY, 1996, 68 (07) :1395-1398