Extended 7,7,8,8-Tetracyano-p-quinodimethane-Based Acceptors: How Molecular Shape and Packing Impact Electron Accepting Behavior

被引:10
作者
Bader, Mamoun M. [1 ]
Pham, Phuong-Truc T. [2 ]
Nassar, Basant R. [1 ]
Lin, Hui [1 ]
Xia, Yu [3 ]
Frisbie, C. Daniel [3 ]
机构
[1] Penn State Univ, Dept Chem, Hazleton, PA USA
[2] Penn State Univ, Dept Chem, Worthington Scranton, PA USA
[3] Univ Minnesota, Dept Chem Engn & Mat Sci, Minneapolis, MN 55455 USA
基金
美国国家科学基金会;
关键词
ELECTROCHEMICAL PROPERTIES; 11,11,12,12-TETRACYANO-9,10-ANTHRAQUINODIMETHANE; DERIVATIVES; CRYSTAL; REDUCTION; PLANARITY; DENSITY;
D O I
10.1021/cg900939c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Structural analysis of pi-extended 7,7,8,8-tetracyano-p-quinodimethane (TCNQ)-based molecules reveal molecular and packing features which may help better understand the weak electron accepting features for these molecules compared with TCNQ. in Solution (cyclic voltammetry measurements), while showing varying trends in thin solid films (photoinduced electron transfer measurements). On the basis of the current findings, we propose that unsymmetrical compounds in this series hold promise as good candidates for use in solar cell applications as their molecular features allow for better solid-state packing, a property likely conducive for better charge transport. Electron acceptor/donor pairs of compatible molecular shapes rather than the usually sought planar shapes may offer a route worth pursuing.
引用
收藏
页码:4599 / 4601
页数:3
相关论文
共 30 条
[1]   7,7,8,8-TETRACYANOQUINODIMETHANE AND ITS ELECTRICALLY CONDUCTING ANION-RADICAL DERIVATIVES [J].
ACKER, DS ;
HARDER, RJ ;
HERTLER, WR ;
MAHLER, W ;
MELBY, LR ;
BENSON, RE ;
MOCHEL, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (24) :6408-6409
[2]  
[Anonymous], ADV POLYM SC
[3]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[4]  
BECKE AD, 2006, SPARTAN 06
[5]   NEW ELECTRON-ACCEPTORS - SYNTHESIS, ELECTROCHEMISTRY, AND RADICAL-ANIONS OF N,7,7-TRICYANOQUINOMETHANIMINES AND X-RAY CRYSTAL-STRUCTURES OF THE TRIMETHYL AND TETRAMETHYL DERIVATIVES [J].
BRYCE, MR ;
DAVIES, SR ;
GRAINGER, AM ;
HELLBERG, J ;
HURSTHOUSE, MB ;
MAZID, M ;
BACHMANN, R ;
GERSON, F .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1690-1696
[6]   New push-pull chromophores featuring TCAQ (11,11,12,12-tetracyano-9,10-anthraquinodimethane) and other dicyanovinyl acceptors [J].
Bures, Filip ;
Schweizer, W. Bernd ;
Boudon, Corinne ;
Gisselbrecht, Jean-Paul ;
Gross, Maurice ;
Diederich, Francois .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (06) :994-1004
[7]   Spectroscopic signatures of spin-charge separation in the quasi-one-dimensional organic conductor TTF-TCNQ -: art. no. 096402 [J].
Claessen, R ;
Sing, M ;
Schwingenschlögl, U ;
Blaha, P ;
Dressel, M ;
Jacobsen, CS .
PHYSICAL REVIEW LETTERS, 2002, 88 (09) :964021-964024
[8]   NOVEL PI-EXTENDED THIOPHENE-FUSED ELECTRON-ACCEPTORS FOR ORGANIC METALS [J].
DELACRUZ, P ;
MARTIN, N ;
MIGUEL, F ;
SEOANE, C ;
ALBERT, A ;
CANO, FH ;
GONZALEZ, A ;
PINGARRON, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6192-6198
[9]   TTF and TCNQ analogues derived from a new benzo-fused thiopyranyl building block [J].
Duan, Zhiming ;
Wei, Zhongming ;
Xu, Wei ;
Zhu, Daoben .
TETRAHEDRON LETTERS, 2009, 50 (21) :2597-2600
[10]   The first two decades of a versatile electron acceptor building block:: 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) [J].
Gomez, Rafael ;
Seoane, Carlos ;
Segura, Jose L. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (08) :1305-1322