1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene: A Precursor for a New Low Band Gap Polymer

Michael Hanack; Ulrich Schmid; Ursula Röhrig; Jean‐Marc ‐M Toussaint; Christine Adant; Jean‐Luc ‐L Brédas

doi:10.1002/cber.19931260633

1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene: A Precursor for a New Low Band Gap Polymer

Michael Hanack^*, Ulrich Schmid, Ursula Röhrig, Jean‐Marc ‐M Toussaint, Christine Adant, Jean‐Luc ‐L Brédas

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐thieno‐[3,4‐c]thiophene(9), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1H,3H1‐thieno[3,4‐c]thiophene 2‐oxide (7) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9. The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.

Original language	English (US)
Pages (from-to)	1487-1491
Number of pages	5
Journal	Chemische Berichte
Volume	126
Issue number	6
DOIs	https://doi.org/10.1002/cber.19931260633
State	Published - Jun 1993
Externally published	Yes

Keywords

1H,3H1‐Thieno[3,4‐c]thiophene derivative
Polyarenemethylenes
Polymers, low band gap

ASJC Scopus subject areas

General Chemistry

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10.1002/cber.19931260633

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title = "1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene: A Precursor for a New Low Band Gap Polymer",

abstract = "A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐thieno‐[3,4‐c]thiophene(9), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1H,3H1‐thieno[3,4‐c]thiophene 2‐oxide (7) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9. The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.",

keywords = "1H,3H1‐Thieno[3,4‐c]thiophene derivative, Polyarenemethylenes, Polymers, low band gap",

author = "Michael Hanack and Ulrich Schmid and Ursula R{\"o}hrig and Toussaint, {Jean‐Marc ‐M} and Christine Adant and Br{\'e}das, {Jean‐Luc ‐L}",

year = "1993",

month = jun,

doi = "10.1002/cber.19931260633",

language = "English (US)",

volume = "126",

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AU - Hanack, Michael

AU - Schmid, Ulrich

AU - Röhrig, Ursula

AU - Toussaint, Jean‐Marc ‐M

AU - Adant, Christine

AU - Brédas, Jean‐Luc ‐L

PY - 1993/6

Y1 - 1993/6

N2 - A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐thieno‐[3,4‐c]thiophene(9), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1H,3H1‐thieno[3,4‐c]thiophene 2‐oxide (7) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9. The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.

AB - A new precursor, 1,3‐bis(2‐thienylmethylene)1‐1H,3H1‐thieno‐[3,4‐c]thiophene(9), for polyarenemethylenes (PAM), which are predicted to be low band gap polymers, is obtained by a Knoevenagel‐type condensation of 1H,3H1‐thieno[3,4‐c]thiophene 2‐oxide (7) with 2‐thiophenecarbaldehyde followed by reduction of the intermediate sulfoxide 8 with 2‐chloro‐1,3,2‐benzodioxaphosphole. Several investigations with cyclic voltammetry and UV‐Vis‐NIR spectroelectrochemistry (SEC) are carried out on 9. The experimental data are compared with the results of electronic band structure calculated on the basis of an MNDO‐optimized geometric structure by VEH pseudopotential method.

KW - 1H,3H1‐Thieno[3,4‐c]thiophene derivative

KW - Polyarenemethylenes

KW - Polymers, low band gap

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SN - 0009-2940

VL - 126

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JO - Chemische Berichte

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ER -

1,3‐Bis(2‐thienylmethylene)1‐1H,3H1‐thieno[3,4‐c]thiophene: A Precursor for a New Low Band Gap Polymer

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Keywords

ASJC Scopus subject areas

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