Amide-bridged ladder poly(p-phenylene): synthesis by direct arylation and π-stacked assembly

被引：11

作者：

Takagi, K. ^{[1
]}

Kato, R. ^{[1
]}

Yamamoto, S. ^{[1
]}

Masu, H. ^{[2
]}

机构：

[1] Nagoya Inst Technol, Dept Mat Sci & Engn, Nagoya, Aichi 4668555, Japan

[2] Chiba Univ, Ctr Analyt Instrumentat, Chiba, Chiba 2638522, Japan

来源：

POLYMER CHEMISTRY | 2015年 / 6卷 / 38期

关键词：

EFFICIENT SYNTHESIS; OPTICAL-PROPERTIES; POLYMERS; ARENES; OLIGOTHIOPHENE; CHROMOPHORES; DERIVATIVES; CYCLIZATION; OLIGOMERS;

D O I：

10.1039/c5py01154j

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Amide-bridged ladder poly(p-phenylene) was synthesized in two steps, through the polycondensation of aromatic diamines and dicarboxylic acid derivatives followed by palladium-catalyzed intramolecular direct arylation. The pi-stacked assembly of the polymer in solution was investigated along with the single crystal X-ray structure analysis of a model oligomer.

引用

页码：6792 / 6795

页数：4

共 43 条

[1] STEREOCHEMISTRIES OF AROMATIC N-METHYLAMIDES IN CRYSTAL AND SOLUTION - TEMPERATURE-DEPENDENT CONFORMATIONAL CONVERSION AND ATTRACTING AROMATIC-AROMATIC INTERACTIONS [J].

AZUMAYA, I ;

KAGECHIKA, H ;

YAMAGUCHI, K ;

SHUDO, K .

TETRAHEDRON, 1995, 51 (18) :5277-5290

[2] High electron mobility in ladder polymer field-effect transistors [J].

Babel, A ;

Jenekhe, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13656-13657

[3] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].

Campeau, LC ;

Parisien, M ;

Jean, A ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590

[4] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].

Campeau, LC ;

Parisien, M ;

Leblanc, M ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187

[5] Synthesis of Fully Soluble Azomethine-Bridged Ladder-Type Poly(p-phenylenes) by Bischler-Napieralski Reaction [J].

Chen, Yulan ;

Huang, Weiguo ;

Li, Chihong ;

Bo, Zhishan .

MACROMOLECULES, 2010, 43 (24) :10216-10220

[6] Dithienylbenzodipyrrolidone: New Acceptor for Donor-Acceptor Low Band Gap Polymers [J].

Cui, Weibin ;

Wudl, Fred .

MACROMOLECULES, 2013, 46 (18) :7232-7238

[7] Dual fluorescence and intramolecular charge transfer with N-phenylphenanthridinones [J].

Demeter, A ;

Bérces, T ;

Zachariasse, KA .

JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (19) :4611-4621

[8] Synthesis and Characterization of Solution-Processable Ladderized n-Type Naphthalene Bisimide Copolymers for OFET Applications [J].

Durban, Matthew M. ;

Kazarinoff, Peter D. ;

Segawa, Yukari ;

Luscombe, Christine K. .

MACROMOLECULES, 2011, 44 (12) :4721-4728

[9] Hydrogen-Bonded Semiconducting Pigments for Air-Stable Field-Effect Transistors [J].

Glowacki, Eric Daniel ;

Irimia-Vladu, Mihai ;

Kaltenbrunner, Martin ;

Gasiorowski, Jacek ;

White, Matthew S. ;

Monkowius, Uwe ;

Romanazzi, Giuseppe ;

Suranna, Gian Paolo ;

Mastrorilli, Piero ;

Sekitani, Tsuyoshi ;

Bauer, Siegfried ;

Someya, Takao ;

Torsi, Luisa ;

Sariciftci, Niyazi Serdar .

ADVANCED MATERIALS, 2013, 25 (11) :1563-1569

[10] Oligomers and polymers based on bridged phenylenes as electronic materials [J].

Grimsdale, Andrew C. ;

Muellen, Klaus .

MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (17) :1676-1702

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