Oxacycle-Fused [1]Benzothieno[3,2-b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure

被引：9

作者：

Mohankumar, Meera ^{[1
]}

Chattopadhyay, Basab ^{[1
]}

Hadji, Rachid ^{[2
]}

Sanguinet, Lionel ^{[2
]}

Kennedy, Alan R. ^{[3
]}

Lemaur, Vincent ^{[4
]}

Cornil, Jerome ^{[4
]}

Fenwick, Oliver ^{[5
]}

Samori, Paolo ^{[5
]}

Geerts, Yves ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Fac Sci, Lab Chim Polymeres, CP 206-1,Blvd Triomphe, B-1050 Brussels, Belgium

[2] Univ Angers, LUNAM Univ, MOLTECH Anjou UMRCNRS 6200, 2 Bd Lavoisier, F-49045 Angers, France

[3] Univ Strathclyde, Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[4] Univ Mons UMons, Serv Chim Mat Nouveaux, Pl Parc 20, B-7000 Mons, Belgium

[5] Univ Strasbourg, CNRS, ISIS, 8 Allee Gaspard Monge, F-67000 Strasbourg, France

来源：

CHEMPLUSCHEM | 2019年 / 84卷 / 09期

关键词：

arenes; crystal engineering; electrochemistry; electronic properties; pi-conjugation; FIELD-EFFECT TRANSISTORS; ORGANIC SINGLE-CRYSTALS; CHARGE-CARRIER MOBILITY; HIGH-PERFORMANCE; SEMICONDUCTOR; TRANSPORT; EXTRACTION; STABILITY; STATE;

D O I：

10.1002/cplu.201800346

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The molecular properties of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) are vulnerable to structural modifications, which in turn are determined by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Fourfold hydroxy-substituted BTBT is the key intermediate, from which the compounds 2,3,7,8-bis(ethylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene and 2,3,7,8-bis(methylenedioxy)-[1]benzothieno[3,2-b][1]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards pi-stacked columns in the newly synthesized derivatives. The results are further justified by the simulated HOMO levels of the model compound.

引用

页码：1263 / 1269

页数：7