Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study
Derivatives of diphenyl-diketo-pyrrolopyrrole, possessing electron-donating or withdrawing groups in the p-position of the phenyl, were synthesized and studied using optical characterization (absorption, fluorescence, time-resolved fluorescence) and quantum chemical calculation. An increase in absor...
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Published in | Dyes and pigments Vol. 84; no. 2; pp. 176 - 182 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
01.02.2010
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Subjects | |
Online Access | Get full text |
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Summary: | Derivatives of diphenyl-diketo-pyrrolopyrrole, possessing electron-donating or withdrawing groups in the
p-position of the phenyl, were synthesized and studied using optical characterization (absorption, fluorescence, time-resolved fluorescence) and quantum chemical calculation. An increase in absorption coefficient ≥10
5 dm
3 mol
−1 cm
−1 was observed using electron–donor groups; a bathochromic shift in both absorption and luminescence peaks was observed as a result of increased conjugation. Soluble derivatives were obtained by the introduction of alkyl groups (by N-alkylation) in the central pyrrolopyrrole unit. Calculated phenyl torsion angles using HF and B3LYP methods showed that the loss of molecule planarity reduced the extent of overlap between the π-orbitals of the central pyrrolopyrrole unit and phenyls after N-alkylation. This treatment thus reduced both the bathochromic shift and increased absorption coefficient. The presence of the donor or acceptor groups in itself does not influence molecule planarity. |
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Bibliography: | ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 |
ISSN: | 0143-7208 1873-3743 |
DOI: | 10.1016/j.dyepig.2009.07.014 |