Substituent and counterion effects on the formation of π-dimer dications of end-capped heptathienoacenes

被引：13

作者：

Capel Ferron, Cristina ^{[1
]}

Ruiz Delgado, M. Carmen ^{[1
]}

Hernandez, Victor ^{[1
]}

Lopez Navarrete, Juan T. ^{[1
]}

Vercelli, Barbara ^{[2
]}

Zotti, Gianni ^{[2
]}

Capdevila Cortada, Marcal ^{[3
,4
]}

Novoa, Juan J. ^{[3
,4
]}

Niu, Weijun ^{[5
]}

He, Mingqian ^{[5
]}

Hartl, Frantisek ^{[6
]}

机构：

[1] Univ Malaga, Dept Quim Fis, E-29071 Malaga, Spain

[2] Inst Energet & Interphases IENI CNR, I-35127 Padua, Italy

[3] Univ Barcelona, Fac Quim, Dept Quim Fis, E-08028 Barcelona, Spain

[4] Univ Barcelona, Fac Quim, IQTCUB, E-08028 Barcelona, Spain

[5] Corning Inc, Corning, NY 14830 USA

[6] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 47期

关键词：

CATION RADICALS; ORGANIC SEMICONDUCTORS; 7; RINGS; OLIGOTHIOPHENES; 3,4-DIBUTYL-2,5-DIPHENYL-2,25,2-TERTHIOPHENE; DIMERIZATION;

D O I：

10.1039/c1cc14566e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have investigated the impact of the functionalization and the chemical nature of counterions on the pi-dimer dications formation in two end-capped heptathienoacenes. Radical cations of an alpha-substituted heptathienoacene with triisopropylsilyl groups do not pi-dimerize, while those of an alpha,beta-substituted heptathienoacene with four n-decyl side chains show a high propensity toward pi-dimerization, increased by PF(6)(-) counterions.

引用

页码：12622 / 12624

页数：3

共 20 条

[1] 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

[2] Neutral and Oxidized Triisopropylsilyl End-Capped Oligothienoacenes: A Combined Electrochemical, Spectroscopic, and Theoretical Study [J].

Arago, Juan ;

Viruela, Pedro M. ;

Orti, Enrique ;

Osuna, Reyes Malave ;

Vercelli, Barbara ;

Zotti, Gianni ;

Hernandez, Victor ;

Lopez Navarrete, Juan T. ;

Henssler, John T. ;

Matzger, Adam J. ;

Suzuki, Yoshitake ;

Yamaguchi, Shigehiro .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5481-5491

[3]

BAUERLE P, 1993, J AM CHEM SOC, V115, P10217

[4] Organic semiconductors:: A theoretical characterization of the basic parameters governing charge transport [J].

Brédas, JL ;

Calbert, JP ;

da Silva, DA ;

Cornil, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (09) :5804-5809

[5] Two-dimensional structural motif in thienoacene semiconductors: Synthesis, structure, and properties of tetrathienoanthracene isomers [J].

Brusso, Jaclyn L. ;

Hirst, Oliver D. ;

Dadvand, Afshin ;

Ganesan, Srinivasan ;

Cicoira, Fabio ;

Robertson, Craig M. ;

Oakley, Richard T. ;

Rosei, Federico ;

Perepichkat, Dmitrii F. .

CHEMISTRY OF MATERIALS, 2008, 20 (07) :2484-2494

[6] STOICHIOMETRIC CONTROL OF THE SUCCESSIVE GENERATION OF THE RADICAL CATION AND DICATION OF EXTENDED ALPHA-CONJUGATED OLIGOTHIOPHENES - A QUANTITATIVE MODEL FOR DOPED POLYTHIOPHENE [J].

FICHOU, D ;

HOROWITZ, G ;

XU, B ;

GARNIER, F .

SYNTHETIC METALS, 1990, 39 (02) :243-259

[7] Single-crystal X-ray structure of the cation radical of 3',4'-dibutyl-2,5''-diphenyl-2,2':5',2''-terthiophene: Definitive evidence for pi-stacked oxidized oligothiophenes [J].

Graf, DD ;

Campbell, JP ;

Miller, LL ;

Mann, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5480-5481

[8] From monomers to pi-stacks. A comprehensive study of the structure and properties of monomeric, pi-dimerized, and pi-stacked forms of the cation radical of 3',4'-dibutyl-2,5''-diphenyl-2,2':5',2''-terthiophene [J].

Graf, DD ;

Duan, RG ;

Campbell, JP ;

Miller, LL ;

Mann, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) :5888-5899

[9] Synthesis and structure of alkyl-substituted fused thiophenes containing up to seven rings [J].

He, Mingqian ;

Zhang, Feixia .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :442-451

[10] Structural control of the reversible dimerization of π-conjugated oligomeric cation radicals [J].

Levillain, E ;

Roncali, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8760-8765

← 1 2 →