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

Osken, Ipek; ŞAHİN, ONUR; Gundogan, Ali S.; Bildirir, Hakan; Capan, Asli; Ertas, Erdal; Eroglu, Mehmet S.; Wallis, John D.; Topal, Kevser; Ozturk, Turan

doi:10.1016/j.tet.2011.11.059

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

Yazarlar (10)

Ipek Osken
İstanbul Teknik Üniversitesi, Türkiye

Prof. Dr. Onur ŞAHİN İstanbul Teknik Üniversitesi, Türkiye

Ali S. Gundogan
İstanbul Teknik Üniversitesi, Türkiye

Hakan Bildirir
İstanbul Teknik Üniversitesi, Türkiye

Asli Capan
İstanbul Teknik Üniversitesi, Türkiye

Dr. Öğr. Üyesi Erdal Ertas Tubıtak Marmara Research Center, Türkiye

Mehmet S. Eroglu
Tübitak Ulusal Metroloji Enstitüsü, Türkiye

John D. Wallis
Nottingham Trent University, İngiltere

Kevser Topal
Tübitak Ulusal Metroloji Enstitüsü, Türkiye

Prof. Dr. Turan Ozturk İstanbul Teknik Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Tetrahedron (Q2)
Dergi ISSN	0040-4020 Dergi Bilgileri (2012)
Makale Dili	İngilizce	Basım Tarihi	01-2012
Cilt / Sayı / Sayfa	68 / 4 / 1216–1222	DOI	10.1016/j.tet.2011.11.059
Makale Linki	http://www.scopus.com/inward/record.url?eid=2-s2.0-84855457402&partnerID=MN8TOARS
UAK Araştırma Alanları	Fen Bilimleri ve Matematik

Özet

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. © 2011 Elsevier Ltd. All rights reserved.

Anahtar Kelimeler

Dithienothiophene | Ethylenedioxythiophene | Phosphorus decasulfide (P 4S 10) | Vinylenedithiathiophene

Science Direct

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	19

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

Dergi Adı	TETRAHEDRON
Kısa Adı	TETRAHEDRON
Yayıncı	PERGAMON-ELSEVIER SCIENCE LTD
Açık Erişim	Hayır
ISSN	0040-4020
E-ISSN	1464-5416
Wos Quartile	Q2
Scopus Quartile	Q1
Tarandığı Indeksler	SCIE , Scopus
WoS Kategoriler	CHEMISTRY, ORGANIC
Scopus Kategoriler	DRUG DISCOVERY \| ORGANIC CHEMISTRY \| BIOCHEMISTRY

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

Paylaş