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Highly Conductive Organic Charge Transfer Complex 1,1,2',2' Bis (1,2 Dithiacyclopentenyl) Ethylene + Electron Acceptor

IP.com Disclosure Number: IPCOM000082891D
Original Publication Date: 1975-Feb-01
Included in the Prior Art Database: 2005-Feb-28
Document File: 1 page(s) / 12K

Publishing Venue

IBM

Related People

Fukushima, AA: AUTHOR [+3]

Abstract

Remarkable electrical conductivity has been observed in charge-transfer systems formed between 1,1,2',2'-bis(l,2-dithiacyclopentenyl) ethylene, a carbocyclic derivative of tetrathiofulvalene (TTF), and suitable electron acceptor molecules such as tetracyanoquinodimethane (TCNQ). Single crystal samples of the cyclopentenyl carbocycle TCNQ complex have been measured, with room temperature conductivities of approximately Eta (rt) = 500 Omega /-1/ cm/-1/. Thus the title system constitutes the first example of a carbocyclic tetrathiofulvalene derivative forming a highly conducting charge-transfer complex. This system is a unique derivative of TTF in the sense that various substitutions in both rings are now possible, some of which are believed potentially better conductors than the title system.

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Highly Conductive Organic Charge Transfer Complex 1,1,2',2' Bis (1,2 Dithiacyclopentenyl) Ethylene + Electron Acceptor

Remarkable electrical conductivity has been observed in charge-transfer systems formed between 1,1,2',2'-bis(l,2-dithiacyclopentenyl) ethylene, a carbocyclic derivative of tetrathiofulvalene (TTF), and suitable electron acceptor molecules such as tetracyanoquinodimethane (TCNQ). Single crystal samples of the cyclopentenyl carbocycle TCNQ complex have been measured, with room temperature conductivities of approximately Eta (rt) = 500 Omega /-1/ cm/-1/. Thus the title system constitutes the first example of a carbocyclic tetrathiofulvalene derivative forming a highly conducting charge-transfer complex. This system is a unique derivative of TTF in the sense that various substitutions in both rings are now possible, some of which are believed potentially better conductors than the title system.

The tetrathiofulvalene derivative (mp 240 d.) was prepared by oxidative coupling of trithiocarbonate (mp 107-8 d.) via the perchlorate salt. Precursor thiocarbonate was obtained by cyclo-sulfurization of intermediate xanthate ester. Xanthate was itself prepared from commercially available Eta - chlorocyclopentanone on treatment with potassium 0-alkyl xanthate.

Solutions of the carbocyclic TTF derivative in refluxing chloroform or tetrachloroethylene afforded the black microcrystalline charge-transfer complex (mp 216 d.), on treatment with mole equivalent solut...