Conjugated Polymers from Naphthalene Bisimide

被引:321
作者
Guo, Xugang [1 ]
Watson, Mark D. [1 ]
机构
[1] Univ Kentucky, Dept Chem, Lexington, KY 40506 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/ol801918y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stille coupling of regioisomerically pure dibromonaphthalene bisimides (NBI) with various stannylated thiophene-based monomers yields (very) high molecular weight donor-acceptor conjugated polymers. Electrochemical and optical absorption measurements reveal that LUMO energies are essentially invariant and dictated by the NBI units, while HOMO energies are dictated by the thienyl comonomers. Optical energy gaps ranging from 1.7 to 1.1 eV are thus obtained. The polymers are also characterized by differential scanning calorimetry and fiber WAXD.
引用
收藏
页码:5333 / 5336
页数:4
相关论文
共 33 条
[1]  
Asawapirom U, 2002, SYNTHESIS-STUTTGART, P1136
[2]   Exploration of the Stille coupling reaction for the syntheses of functional polymers [J].
Bao, ZN ;
Chan, WK ;
Yu, LP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (50) :12426-12435
[3]   Toward a rational design of poly(2,7-carbazole) derivatives for solar cells [J].
Blouin, Nicolas ;
Michaud, Alexandre ;
Gendron, David ;
Wakim, Salem ;
Blair, Emily ;
Neagu-Plesu, Rodica ;
Belletete, Michel ;
Durocher, Gilles ;
Tao, Ye ;
Leclerc, Mario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) :732-742
[4]   Density functional theory (B3LYP/6-31G*) study of oligothiophenes in their aromatic and polaronic states [J].
Bouzzine, SM ;
Bouzakraoui, S ;
Bouachrine, M ;
Hamidi, M .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2005, 726 (1-3) :271-276
[5]   Very large acceleration of the photoinduced electron transfer in a Ru(bpy)3-naphthalene bisimide dyad bridged on the naphthyl core [J].
Chaignon, Frederique ;
Falkenstrom, Magnus ;
Karlsson, Susanne ;
Blart, Errol ;
Odobel, Fabrice ;
Hammarstrom, Leif .
CHEMICAL COMMUNICATIONS, 2007, (01) :64-66
[6]   Syntheses and properties of core-substituted naphthalene bisimides with aryl ethynyl or cyano groups [J].
Chopin, Stephanie ;
Chaignon, Frederique ;
Blart, Errol ;
Odobel, Fabrice .
JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (39) :4139-4146
[7]   Solid-state packing of conjugated oligomers:: from π-stacks to the herringbone structure [J].
Curtis, MD ;
Cao, J ;
Kampf, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4318-4328
[8]   A hybrid polymer of polyaniline and phthalimide dyes [J].
Dierschke, F ;
Jacob, J ;
Müllen, K .
SYNTHETIC METALS, 2006, 156 (5-6) :433-443
[9]   Low-oxidation-potential conducting polymers derived from 3,4-ethylenedioxythiophene and dialkoxybenzenes [J].
Irvin, JA ;
Schwendeman, I ;
Lee, Y ;
Abboud, KA ;
Reynolds, JR .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2001, 39 (13) :2164-2178
[10]   Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport [J].
Jones, Brooks A. ;
Facchetti, Antonio ;
Wasielewski, Michael R. ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15259-15278