Synthesis of Polymers Possessing Tetraphenylethylene Units by Three-Component Coupling Reactions of Poly(p-phenylene ethynylene) Derivative with Aryl Halides and Phenylboronic Acid

被引：0

作者：

Suto, Takeru ^{[1
]}

Nishiyama, Hiroki ^{[1
]}

Inagi, Shinsuke ^{[1
]}

Tomita, Ikuyoshi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2015年 / 53卷 / 06期

关键词：

conjugated polymers; functionalization of polymers; synthesis; DONOR-ACCEPTOR CHROMOPHORES; CONJUGATED POLYMERS; TETRASUBSTITUTED OLEFINS; OPTICAL-PROPERTIES; LIGHT; POLY(ARYLENEETHYNYLENE)S; EFFICIENT; DEVICES; DIODES; ROUTE;

D O I：

10.1002/pola.27503

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

A derivative of poly(p-phenylene ethynylene) was subjected to the palladium-catalyzed three-component coupling reactions with aryl halides and phenylboronic acid to obtain polymers having tetrasubstituted cis-vinylene units. For example, 69% of the acetylene units in the prepolymer were converted to cis-vinylene (i.e., tetrasubstituted cis-vinylene) units using iodobenzene and phenylboronic acid (5 equiv each with respect to acetylene units). In the UV-vis absorption spectra of the resulting polymers, clear hypsochromic shifts of the absorption maxima were observed, while bathochromic shifts and suppression of the efficiency were observed in their photoluminescence spectra. (C) 2015 Wiley Periodicals, Inc.

引用

收藏

页码：787 / 791

页数：5

相关论文

共 29 条

[1] VISIBLE-LIGHT EMISSION FROM SEMICONDUCTING POLYMER DIODES [J].

BRAUN, D ;

HEEGER, AJ .

APPLIED PHYSICS LETTERS, 1991, 58 (18) :1982-1984

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

Bunz, UHF .

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

[3] LIGHT-EMITTING-DIODES BASED ON CONJUGATED POLYMERS [J].

BURROUGHES, JH ;

BRADLEY, DDC ;

BROWN, AR ;

MARKS, RN ;

MACKAY, K ;

FRIEND, RH ;

BURN, PL ;

HOLMES, AB .

NATURE, 1990, 347 (6293) :539-541

[4]

Diaz A F, 1979, CHEM COMMUN, V14, P635

[5] Ethynylene-containing donor-acceptor alternating conjugated polymers: Synthesis and photovoltaic properties [J].

Du, Chun ;

Li, Weiwei ;

Li, Cuihong ;

Bo, Zhishan .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (02) :383-393

[6] Conjugated Polymers for the Fluorescent Detection of Nitroaromatics: Influence of Side-Chain Sterics and π-System Electronics [J].

Duniho, Tyler L. ;

Laughlin, Brynna J. ;

Buelt, Ashley A. ;

Baker, William F. ;

Conrad, Catherine A. ;

Smith, Rhett C. .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2014, 52 (10) :1487-1492

[7] Electroluminescence in conjugated polymers [J].

Friend, RH ;

Gymer, RW ;

Holmes, AB ;

Burroughes, JH ;

Marks, RN ;

Taliani, C ;

Bradley, DDC ;

Dos Santos, DA ;

Brédas, JL ;

Lögdlund, M ;

Salaneck, WR .

NATURE, 1999, 397 (6715) :121-128

[8] High-Yielding Alkyne-Tetracyanoethylene Addition Reactions: A Powerful Tool for Analyzing Alkyne-Linked Conjugated Polymer Structures [J].

Fujita, Hiroyuki ;

Tsuboi, Kazuma ;

Michinobu, Tsuyoshi .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 2011, 212 (16) :1758-1766

[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] All-Donor Poly(arylene-ethynylene)s Containing Anthracene and Silole-Based Units: Synthesis, Electronic, and Photovoltaic Properties [J].

Grisorio, Roberto ;

Suranna, Gian Paolo ;

Mastrorilli, Piero ;

Allegretta, Giovanni ;

Loiudice, Anna ;

Rizzo, Aurora ;

Gigli, Giuseppe ;

Manoli, Kyriaki ;

Magliulo, Maria ;

Torsi, Luisa .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (22) :4860-4872