Synthesis and Properties of Furanyl-Substituted [1]Benzothieno[3,2-b][1]benzothiophene Derivatives

被引：0

作者：

Tolkachev, E. D. ^{[1
]}

Becker, C. S. ^{[1
]}

Sonina, A. A. ^{[1
]}

Kuimov, A. D. ^{[1
]}

Kazantsev, M. S. ^{[1
]}

机构：

[1] Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk, Russia

来源：

CHEMISTRY FOR SUSTAINABLE DEVELOPMENT | 2024年 / 32卷 / 04期

关键词：

1]benzothieno[3; b; [1]benzothiophene; organic electronics; furan; photoluminescence; bromination; ROUTE;

D O I：

10.15372/CSD2024587

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[1]Benzothieno[3,2-b][1]benzothiophene (BTBT) derivatives attract attention in the field of organic optoelectronics due to their stability in air, 2D film formation ability and high charge-carrier mobility. Here we present approaches to the synthesis of new furanyl-substituted BTBT derivatives. The physicochemical properties of the target compounds were studied. It is shown that all materials have high quantum yields of photoluminescence. A thorough analysis of BTBT bromination has been carried out, and the reaction conditions were optimised. It has been shown that a mixture of regioisomers is always formed in this process, but this does not necessarily interfere with further synthesis. A significant reduction in the total reaction time from 48 to 6 hours has been achieved.

引用

页码：528 / 537

页数：10

共 16 条

[1]

[Anonymous], 1991, J AM CHEM SOC, DOI DOI 10.1002/9780470132449.CH23

[2] Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives [J].

Britton, Luke ;

Skrodzki, Maciej ;

Nichol, Gary S. ;

Dominey, Andrew P. ;

Docherty, Jamie H. ;

Thomas, Stephen P. .

ACS CATALYSIS, 2021, 11 (12) :6857-6864

[3]

Chen F. C., 2018, Encyclopedia of Modern Optics, V5, P220

[4] A FACILE ROUTE TO 5-ALKYL-2(3H)-FURANONES BY PHOTO-ISOMERIZATION OF ENEDICARBONYL COMPOUNDS [J].

DAURIA, M ;

DEMICO, A ;

PIANCATELLI, G ;

SCETTRI, A .

TETRAHEDRON, 1982, 38 (11) :1661-1666

[5] Singlet-Oxygen-Initiated Tandem Transformation of 2-Hexylfuran to the Natural Alkaloids Glochidine and Glochidicine [J].

Ioannou, Georgios I. ;

Kalaitzakis, Dimitris ;

Vassilikogiannakis, Georgios .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) :3304-3306

[6] Reactivity of [1]benzothieno[3,2-b][1]benzothiophene -: Electrophilic and metallation reactions [J].

Kosata, B ;

Kozmík, V ;

Svoboda, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2002, 67 (05) :645-664

[7] A quantitative topological descriptor for linear co-oligomer fusion [J].

Koskin, Igor P. ;

Mostovich, Evgeny A. ;

Benassi, Enrico ;

Kazantsev, Maxim S. .

CHEMICAL COMMUNICATIONS, 2018, 54 (52) :7235-7238

[8] 2,6-Dibromogallates as a new building block for controlling π-stacking, network formation and mirror symmetry breaking [J].

Kwon, Ohjin ;

Cai, Xiaoqian ;

Saeed, Azhar ;

Liu, Feng ;

Poppe, Silvio ;

Tschierske, Carsten .

CHEMICAL COMMUNICATIONS, 2021, 57 (53) :6491-6494

[9] BENZANNULATION OF AROMATIC HETEROCYCLES - A REGIOCONTROLLED METHOD FOR CONSTRUCTION OF SUBSTITUTED BENZOFURANS AND DIBENZOFURANS AND BENZOTHIOPHENES AND DIBENZOTHIOPHENES [J].

LIEBESKIND, LS ;

WANG, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (13) :3550-3556

[10] Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers [J].

Lik, Artur ;

Fritze, Lars ;

Mueller, Lars ;

Helten, Holger .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (16) :5692-5695

← 1 2 →