Reduced band gap dithieno[3,2-b:2′,3′-d]pyrroles:: New n-type organic materials via unexpected reactivity

被引：59

作者：

Pappenfus, Ted M. ^{[1
]}

Hermanson, Bethany J. ^{[1
]}

Helland, Tyler J. ^{[1
]}

Lee, Garett G. W. ^{[1
]}

Drew, Steven M.

Mann, Kent R. ^{[2
]}

McGee, Kari A. ^{[2
]}

Rasmussen, Seth C. ^{[3
]}

机构：

[1] Univ Minnesota, Div Sci & Math, Morris, MN 56267 USA

[2] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

[3] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 08期

关键词：

D O I：

10.1021/ol8002018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct addition of tetracyanoethylene to N-(p-hexylphenyl)dithieno[3,2-6:2',3'-d]pyrrole yields not only the aromatic mono- and bis-tricyanovinyl-substituted products but also a quinoidal product with dicyanomethylene groups. The analogous reaction with dithieno[3,2-b:2',3'-d]thiophene yields exclusively the aromatic mono-tricyanovinyl product. The aromatic and quinoidal products possess red-shifted absorptions, increased electron affinities, and favorable pi-stacking motifs in comparison to the unsubstituted oligomers.

引用

页码：1553 / 1556

页数：4

共 32 条

[1] Tricyanovinyl-substituted oligothiophenes [J].

Bader, MM ;

Custelcean, R ;

Ward, MD .

CHEMISTRY OF MATERIALS, 2003, 15 (03) :616-618

[2] Adsorption of carboxyl-terminated dithiophene and terthiophene molecules on ITO electrodes and their electrochemical coupling to polymer layers. The influence of molecular geometry [J].

Berlin, A ;

Zotti, G ;

Schiavon, G ;

Zecchin, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13453-13460

[3] 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

[4] A novel approach to synthesis of tricyanovinylthiophene for heterocyclic imidazole nonlinear optical chromophores [J].

Bu, XR ;

Li, HY ;

VanDerveer, D ;

Mintz, EA .

TETRAHEDRON LETTERS, 1996, 37 (41) :7331-7334

[5] Donor-acceptor-substituted phenylethenyl bithiophenes:: Highly efficient and stable nonlinear optical chromophores [J].

Cai, CZ ;

Liakatas, I ;

Wong, MS ;

Bösch, M ;

Bosshard, C ;

Gunter, P ;

Concilio, S ;

Tirelli, N ;

Suter, UW .

ORGANIC LETTERS, 1999, 1 (11) :1847-1849

[6] N- and P-channel transport behavior in thin film transistors based on tricyanovinyl-capped oligothiophenes [J].

Cai, Xiuyu ;

Burand, Michael W. ;

Newman, Christopher R. ;

da Silva Filho, Demetrio A. ;

Pappenfus, Ted M. ;

Bader, Mamoun M. ;

Bredas, Jean-Luc ;

Mann, Kent R. ;

Frisbie, C. Daniel .

JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (30) :14590-14597

[7] Exploration of ground and excited electronic states of aromatic and quinoid S,S-dioxide terthiophenes.: Complementary systems for enhanced electronic organic materials [J].

Casado, Juan ;

Zgierski, Marek Z. ;

Ewbank, Paul C. ;

Burand, Michael W. ;

Janzen, Daron E. ;

Mann, Kent R. ;

Pappenfus, Ted M. ;

Berlin, Anna ;

Perez-Inestrosa, Ezequiel ;

Ortiz, Rocio Ponce ;

Navarrete, Juan T. Lopez .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10134-10144

[8] Optical, redox, and NLO properties of tricyanovinyl oligothiophenes:: Comparisons between symmetric and asymmetric substitution patterns [J].

Casado, Juan ;

Delgado, M. Carmen Ruiz ;

Merchan, M. Carmen Rey ;

Hernandez, Victor ;

Navarrete, Juan T. Lopez ;

Pappenfus, Ted M. ;

Williams, Nathaniel ;

Stegner, William J. ;

Johnson, Jared C. ;

Edlund, Brett A. ;

Janzen, Daron E. ;

Mann, Kent R. ;

Orduna, Jesu ;

Villacampa, Belen .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5458-5470

[9] Nitro-functionalized oligothiophenes as a novel type of electroactive molecular material:: Spectroscopic, electrochemical, and computational study [J].

Casaso, J ;

Pappenfus, TM ;

Miller, LL ;

Mann, KR ;

Ortí, E ;

Viruela, PM ;

Pou-Amérigo, R ;

Hernández, V ;

Navarrete, JTL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2524-2534

[10] Soluble star-shaped molecules based on thiophene derivatives as organic semiconductors for field-effect transistor applications [J].

Kim, Kyung Hwan ;

Chi, Zhenguo ;

Cho, Min Ju ;

Jin, Jung-Il ;

Cho, Mi Yeon ;

Kim, Su Jin ;

Joo, Jin-Soo ;

Choi, Dong Hoon .

CHEMISTRY OF MATERIALS, 2007, 19 (20) :4925-4932

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