Selective syntheses of vinylenedithiathiophenes (VDTTs) and dithieno[2,3-b;2′,3′-d]thiophenes (DTTs); Building blocks for π-conjugated systems

Ipek Osken, Onur Sahin, Ali S. Gundogan, Hakan Bildirir, Asli Capan, Erdal Ertas, Mehmet S. Eroglu, John D. Wallis, Kevser Topal, Turan Ozturk*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Selective syntheses of 3,4-vinylenedithiathiophenes (VDTTs) and dithieno[2,3-b;2′,3′-d]thiophenes (DTTs), having Ph, 4-CH 3OC 6H 4, 4-BrC 6H 4, 4-NO 2C 6H 4 and 4-(CH 3) 2NC 6H 4 groups, were achieved through the reaction of 1,8-diketone with phosphorus decasulfide (P 4S 10). The reaction could be shifted between VDTT and DTT by adding base (sodium bicarbonate) or acid (para-toluenesulfonic acid), respectively, to the reaction mixture. While the VDTTs were obtained in moderate yields, an important achievement has been made with the syntheses of the DTTs, obtaining them in higher yields compared with the previous report. Polymers of the VDTTs, which are the analogues of ethylenedioxythiophene, EDOT, were prepared using FeCl 3. Unfortunately, all attempts for their electropolymerization failed. Spin density calculations revealed that none of the VDTTs had a significant positive spin density at the 'α' carbon atoms of the thiophene ring. Considering their solubility and functional groups, which could be further derivatized, they are useful building blocks for the preparation of new organic materials.

Original languageEnglish
Pages (from-to)1216-1222
Number of pages7
JournalTetrahedron
Volume68
Issue number4
DOIs
Publication statusPublished - 28 Jan 2012

Funding

We thank Prof Esma Sezer of ITU for her useful discussions of electrochemical measurements, the UK National Crystallography Service, University of Southampton, for a dataset and Istanbul Technical University, Turkey, The Scientific and Technological Research Council of Turkey (108T941) and Unsped Global Lojistik for financial supports. We acknowledge NationalCenter for High Performance Computing (UYBHM) for the computer time provided.

FundersFunder number
National Crystallography Service
International Technological University
University of Southampton
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu108T941
Istanbul Teknik Üniversitesi

    Keywords

    • Dithienothiophene
    • Ethylenedioxythiophene
    • Phosphorus decasulfide (P S )
    • Vinylenedithiathiophene

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