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Synthesis, Structures, and Properties of Disubstituted Heteroacenes on One Side Containing Both Pyrrole and Thiophene Rings.
- Source :
-
Journal of Organic Chemistry . 6/20/2008, Vol. 73 Issue 12, p4638-4643. 3p. 4 Diagrams, 2 Charts, 2 Graphs. - Publication Year :
- 2008
-
Abstract
- A new series of ladder-type heteroacenes containing both pyrrole and furan rings, 5,6-disubstituted diindolo[3,2-b:4,5-b′]thiophenes (DITs), were effectively synthesized from N-functionalized 3,3′-dibromo- 2,2′-biindoles undergoing intramolecular cyclization with bis(phenylsulfonyl) sulfide and organolithium. Single-crystal X-ray results demonstrate that 5,6-dipropyldiindolo[3,2-b:4,5-b′]thiophene (4b) forms a herringbone-type of packing motif and 5,6-di(p-tolyl)diindolo[3,2-b:4,5-b′]thiophene (4d) forms a parallel packing motif. Both of them have S-S contacts, enhancing the electronic transport between molecules. Their photophysical properties suggest that the skeleton of diindolo[3,2-b:4,5-b′]thiophene is more favorable to aggregate in solid than that of indolo[3,2-b]carbazole. The large band gaps and low-lying HOMO energy levels could result in much better stability. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 73
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32720154
- Full Text :
- https://doi.org/10.1021/jo800622y