Synthesis of Conjugated Polymers Containing Octafluorobiphenylene Unit via Pd-Catalyzed Cross-Dehydrogenative-Coupling Reaction

被引:47
作者
Aoki, Hideaki [1 ]
Saito, Hitoshi [1 ]
Shimoyama, Yuto [1 ]
Kuwabara, Junpei [1 ]
Yasuda, Takeshi [2 ]
Kanbara, Takaki [1 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba Res Ctr Energy Mat Sci TREMS, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058573, Japan
[2] Natl Inst Mat Sci, Res Ctr Funct Mat, 1-2-1 Sengen, Tsukuba, Ibaraki 3050047, Japan
关键词
C-H ARYLATION; DIRECT (HETERO)ARYLATION POLYMERIZATION; HIGH-PERFORMANCE; SIDE REACTIONS; COPOLYMERS; FACILE; ACCESS; POLYFLUOROARENES; THIOPHENES;
D O I
10.1021/acsmacrolett.7b00887
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Polycondensation via Pd-catalyzed cross-dehydrogenative-coupling reaction of 2,2',3,3',5,5',6,6'-octafluorobiphenyl with thiophene analogues was studied. The synthetic protocol, in which employment of prefunctionalized starting monomers was fully avoided, allowed straightforward access to an alternating pi-conjugated polymer. The addition of K2CO3 to the catalytic system promotes the cross-coupling reaction and suppresses the undesired homocoupling reaction, producing the corresponding donor acceptor type pi-conjugated polymers with minor homocoupling defects. The reaction also proceeded using O-2 as the terminal oxidant, resulting in lower loading of the Ag oxidant. The obtained polymer was evaluated as an emitting material for an organic light-emitting diode.
引用
收藏
页码:90 / 94
页数:5
相关论文
共 43 条
[1]   Direct C-H arylation: a "Greener" approach towards facile synthesis of organic semiconducting molecules and polymers [J].
Bohra, Hassan ;
Wang, Mingfeng .
JOURNAL OF MATERIALS CHEMISTRY A, 2017, 5 (23) :11550-11571
[2]   Tin-Free Direct C-H Arylation Polymerization for High Photovoltaic Efficiency Conjugated Copolymers [J].
Dudnik, Alexander S. ;
Aldrich, Thomas J. ;
EasthamP, Nicholas D. ;
Chang, Robert P. H. ;
Facchetti, Antonio ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (48) :15699-15709
[3]   Synthesis of random poly(hexyl thiophene-3-carboxylate) copolymers via oxidative direct arylation polymerization (oxi-DArP) [J].
Gobalasingham, Nemal S. ;
Pankow, Robert M. ;
Thompson, Barry C. .
POLYMER CHEMISTRY, 2017, 8 (12) :1963-1971
[4]   Palladium-catalyzed oxidative direct arylation polymerization (Oxi-DArP) of an ester-functionalized thiophene [J].
Gobalasingham, Nemal S. ;
Noh, Sangtaik ;
Thompson, Barry C. .
POLYMER CHEMISTRY, 2016, 7 (08) :1623-1631
[5]   Robust Direct (Hetero)arylation Polymerization in Biphasic Conditions [J].
Grenier, Francois ;
Goudreau, Karine ;
Leclerc, Mario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (07) :2816-2824
[6]   Oxidative Direct Arylation Polymerization Using Oxygen as the Sole Oxidant: Facile, Green Access to Bithiazole-Based Polymers [J].
Guo, Qiang ;
Wu, Di ;
You, Jingsong .
CHEMSUSCHEM, 2016, 9 (19) :2765-2768
[7]   Rapid Access to 2,2′-Bithiazole-Based Copolymers via Sequential Palladium-Catalyzed C-H/C-X and C-H/C-H Coupling Reactions [J].
Guo, Qiang ;
Jiang, Ruyong ;
Wu, Di ;
You, Jingsong .
MACROMOLECULAR RAPID COMMUNICATIONS, 2016, 37 (09) :794-798
[8]   Palladium Immobilized on Thiol-Modified Silica Gel for Effective Direct C-H Arylation [J].
Hayashi, Shotaro ;
Takigami, Atsushi ;
Koizumi, Toshio .
CHEMPLUSCHEM, 2016, 81 (09) :930-934
[9]   Palladium-Catalyzed Aerobic Dehydrogenative Cross-Coupling of Polyfluoroarenes with Thiophenes: Facile Access to Polyfluoroarene-Thiophene Structure [J].
He, Chun-Yang ;
Min, Qiao-Qiao ;
Zhang, Xingang .
ORGANOMETALLICS, 2012, 31 (04) :1335-1340
[10]   Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles [J].
He, Chun-Yang ;
Fan, Shilu ;
Zhang, Xingang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) :12850-12852