Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/2260
Title: Convenient synthesis and polymerization of 5,6-disubstituted dithiophthalides toward soluble poly(isothianaphthene): An initial spectroscopic characterization of the resulting low-band-gap polymers
Authors: POLEC, Iwona 
HENCKENS, Anja 
GORIS, Ludwig 
NICOLAS, Mael 
Loi, MA
ADRIAENSENS, Peter 
LUTSEN, Laurence 
MANCA, Jean 
VANDERZANDE, Dirk 
Sariciftci, NS
Issue Date: 2003
Publisher: JOHN WILEY & SONS INC
Source: JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 41(7). p. 1034-1045
Abstract: A new synthetic procedure toward substituted dithiophthalides, 5,6-dialkyloxydithiophthalide and 5,6-dithioalkyldithiophthalide, is presented. 5,6-Dithiooctyldithiophthalide was obtained from 4,5-dichlorophthalic acid in an eight-step reaction with an overall yield of 26%. 5,6-Dioctyloxydithiophthalide was obtained from 4,5-dihydroxyphthalic acid dimethyl ester in a seven-step reaction (overall yield 15%). Both monomers were polymerized by a thermal and nonoxidative polymerization that resulted in soluble poly(isothianaphthene) derivatives with a band gap of about 1.2 eV. Photoinduced absorption measurements revealed the existence of charged excitations upon illumination. The photoinduced charge generation, combined with the extensive light-harvesting properties and the easy processability, makes these materials quite promising for photovoltaic applications.
Notes: Limburgs Univ Ctr, Dept Chem & Phys, Mat Res Inst, B-3590 Diepenbeek, Belgium. Johannes Kepler Univ, Dept Phys Chem, Linz Inst Organ Solar Cells, A-4040 Linz, Austria.Vanderzande, D, Limburgs Univ Ctr, Dept Chem & Phys, Mat Res Inst, Univ Campus,Gebouw D, B-3590 Diepenbeek, Belgium.
Keywords: 5,6-dithiooctyldithiophthalide; 5,6-dioctyloxydithiophthalide; synthesis; reductive polymerization; low-band-gap polymers; conjugated polymers; photophysics
Document URI: http://hdl.handle.net/1942/2260
ISSN: 0887-624X
e-ISSN: 1099-0518
DOI: 10.1002/pola.10646
ISI #: 000181413300017
Category: A1
Type: Journal Contribution
Validations: ecoom 2004
Appears in Collections:Research publications

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