Highly Efficient Benzannulation of Poly(phenylene ethynylene)s

被引：49

作者：

Arslan, Hasan ^{[2
]}

Saathoff, Jonathan D. ^{[1
]}

Bunck, David N. ^{[2
]}

Clancy, Paulette ^{[1
]}

Dichtel, William R. ^{[2
]}

机构：

[1] Cornell Univ, Sch Chem & Biomol Engn, Ithaca, NY 14853 USA

[2] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 48期

基金：

美国国家科学基金会;

关键词：

conjugation; cycloaddition; graphene; isotopic labeling; polymers; POLYPHENYLENE DENDRIMERS; CONJUGATED POLYMERS; OLIGOMERS; POLY(ARYLENEETHYNYLENE)S;

D O I：

10.1002/anie.201206964

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Put a ring on it: Sterically congested polyarylenes can be synthesized by benzannulation reactions at each C≡C bond of a poly(phenylene ethynylene) (see picture), one of the most easily synthesized and versatile classes of conjugated polymers. The benzannulation reaction is highly specific and efficient, as determined by an isotopic labeling study and several complementary spectroscopic methods. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12051 / 12054

页数：4

共 36 条

[1] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[2] Facile reduction of poly (2,5-dialkoxy-p-phenylene ethynylene)s:: An efficient route for the synthesis of poly (2,5-dialkoxy-p-xylylene)s [J].

Beck, JB ;

Kokil, A ;

Ray, D ;

Rowan, SJ ;

Weder, C .

MACROMOLECULES, 2002, 35 (03) :590-593

[3] Pyrene as chromophore and electrophore:: Encapsulation in a rigid polyphenylene shell [J].

Bernhardt, Stefan ;

Kastler, Marcel ;

Enkelmann, Volker ;

Baumgarten, Martin ;

Muellen, Klaus .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :6117-6128

[4] Photoproduction of proton gradients with π-stacked fluorophore scaffolds in lipid bilayers [J].

Bhosale, Sheshanath ;

Sisson, Adam L. ;

Talukdar, Pinaki ;

Fuerstenberg, Alexandre ;

Banerji, Natalie ;

Vauthey, Eric ;

Bollot, Guillaume ;

Mareda, Jiri ;

Roger, Cornelia ;

Wuerthner, Frank ;

Sakai, Naomi ;

Matile, Stefan .

SCIENCE, 2006, 313 (5783) :84-86

[5] Poly-orthophenylenes:: Synthesis by Suzuki coupling and solid state helical structures [J].

Blake, AJ ;

Cooke, PA ;

Doyle, KJ ;

Gair, S ;

Simpkins, NS .

TETRAHEDRON LETTERS, 1998, 39 (49) :9093-9096

[6] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[7] Graphene Nanoribbons by Chemists: Nanometer-Sized, Soluble, and Defect-Free [J].

Doessel, Lukas ;

Gherghel, Lileta ;

Feng, Xinliang ;

Muellen, Klaus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) :2540-2543

[8]

Dossel L., 2011, Angew. Chem, V123, P2588

[9] Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices [J].

Grimsdale, Andrew C. ;

Chan, Khai Leok ;

Martin, Rainer E. ;

Jokisz, Pawel G. ;

Holmes, Andrew B. .

CHEMICAL REVIEWS, 2009, 109 (03) :897-1091

[10] Evidence of aggregate formation for 2,5-dialkylpoly(p-phenyleneethynylenes) in solution and thin films [J].

Halkyard, CE ;

Rampey, ME ;

Kloppenburg, L ;

Studer-Martinez, SL ;

Bunz, UHF .

MACROMOLECULES, 1998, 31 (25) :8655-8659

← 1 2 3 4 →