Asymmetric Squaraine Dyes: Spectroscopic and Theoretical Investigation

被引：34
作者：
Shafeekh, K. M. [1 ]
Das, Suresh [1 ]
Sissa, Cristina [2 ,3 ]
Painelli, Anna [2 ,3 ]
机构：
[1] Natl Inst Interdisciplinary Sci & Technol CSIR NI, Chem Sci & Technol Div, Photosci & Photon Sect, Trivandrum 695019, Kerala, India
[2] Univ Parma, Dipartimento Chim, I-43100 Parma, Italy
[3] INSTM UdR Parma, I-43100 Parma, Italy
来源：
JOURNAL OF PHYSICAL CHEMISTRY B | 2013年 / 117卷 / 28期
关键词：
NONLINEAR-OPTICAL PROPERTIES; NEAR-INFRARED ABSORPTION; UNSYMMETRICAL SQUARAINES; SYMMETRY-BREAKING; QUADRUPOLAR CHROMOPHORES; NANOCRYSTALLINE TIO2; ELECTRONIC-STRUCTURE; CHARGE-TRANSFER; SOLAR-CELLS; ONE-PHOTON;
D O I：
10.1021/jp401099g
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：
A joint experimental and theoretical study is presented of two asymmetric squaraine dyes and their parent symmetric dyes. The definition of reliable essential-state models for asymmetric squaraines sheds light on the intriguing spectroscopic behavior of this class of molecules, showing inverted and normal solvatochromism in absorption and emission, respectively. This behavior is related to charge redistribution in the excited state, with important implications for optimal design of asymmetric dyes for solar cell applications.
引用
收藏
页码：8536 / 8546
页数：11
相关论文
共 80 条
[1]   Chemistry of squaraine-derived materials: Near-IR dyes, low band gap systems, and cation sensors [J].
Ajayaghosh, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (06) :449-459
[2]   Dye sensitization of nanocrystalline TiO2:: enhanced efficiency of unsymmetrical versus symmetrical squaraine dyes [J].
Alex, S ;
Santhosh, U ;
Das, S .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 172 (01) :63-71
[3]   Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].
Allard, Sybille ;
Forster, Michael ;
Souharce, Benjamin ;
Thiem, Heiko ;
Scherf, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098
[4]   Squaraine dyes in PDT: from basic design to in vivo demonstration [J].
Avirah, Rekha R. ;
Jayaram, Dhanya T. ;
Adarsh, Nagappanpillai ;
Ramaiah, Danaboyina .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (05) :911-920
[5]   Marked Alkyl- vs Alkenyl-Substitutent Effects on Squaraine Dye Solid-State Structure, Carrier Mobility, and Bulk-Heterojunction Solar Cell Efficiency [J].
Bagnis, Diego ;
Beverina, Luca ;
Huang, Hui ;
Silvestri, Fabio ;
Yao, Yan ;
Yan, Henry ;
Pagani, Giorgio A. ;
Marks, Tobin J. ;
Facchetti, Antonio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) :4074-+
[6]   Quantum mechanical computations and spectroscopy: From small rigid molecules in the gas phase to large flexible molecules in solution [J].
Barone, Vincenzo ;
Improta, Roberto ;
Rega, Nadia .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (05) :605-616
[7]   Fully Integrated Approach to Compute Vibrationally Resolved Optical Spectra: From Small Molecules to Macrosystems [J].
Barone, Vincenzo ;
Bloino, Julien ;
Biczysko, Malgorzata ;
Santoro, Fabrizio .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2009, 5 (03) :540-554
[8]   A squaraine-based chemosensor for Hg2+ and Pb2+ [J].
Basheer, MC ;
Alex, S ;
Thomas, KG ;
Suresh, CH ;
Das, S .
TETRAHEDRON, 2006, 62 (04) :605-610
[9]   Assessment of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers:: Design, synthesis, and characterization [J].
Beverina, Luca ;
Crippa, Maurizio ;
Landenna, Mirko ;
Ruffo, Riccardo ;
Salice, Patrizio ;
Silvestri, Fabio ;
Versari, Silvia ;
Villa, Alessandro ;
Ciaffoni, Luca ;
Collini, Elisabetta ;
Ferrante, Camilla ;
Bradamante, Silvia ;
Mari, Claudio M. ;
Bozio, Renato ;
Pagani, Giorgio A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1894-1902
[10]   Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications [J].
Beverina, Luca ;
Salice, Patrizio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (07) :1207-1225
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