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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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