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Structure, Z/E photoisomerization and an effect of (phenylene-)vinylene conjugation extension on absorption and fluorescence of methylidene-pyrrolinones
Authors: Luňák Stanislav, Jr. | Eliáš Zdeněk | Vyňuchal Jan | Lyčka Antonín | Padělková Zdeňka | Hrdina Radim
Year: 2012
Type of publication: článek v odborném periodiku
Name of source: Journal of Molecular Structure
Publisher name: Elsevier Science BV
Place: Amsterdam
Page from-to: 159-166
Titles:
Language Name Abstract Keywords
cze Struktura, Z/E fotoisomerizace a efekt (fenylen)vinylenové konjugace na absorpci a fluorescenci methyliden-pyrrolinonů Šest methyliden-pyrrolinonů s konjugovaným řetězcem vinylen a fenylen-vinylen skupin bylo studováno: pět z nich bylo připraveno poprvé. Jejich struktuty byly odhadnuty na základě DFT výpočtu a ve dvou případech potvrzeny X-ray difrakcí. Strukturní změny Z/E fotoisomerizace v roztoku byly studovány kombinací 1H NMR a DFT CIAO metodou. Oba typy konjugace způsobují bathochromní posun absorpce světla. Prodloužení vinylenu způsobilo fluorescenční chování v roztoku. N-methyl deriváty vykazují fluorescenci v pevném stavu. Struktura; Z/E; fotoisomerizace; fenylen; vinylen; konjugace; absorpce; fluorescence; methyliden-pyrrolinony
eng Structure, Z/E photoisomerization and an effect of (phenylene-)vinylene conjugation extension on absorption and fluorescence of methylidene-pyrrolinones Six methylidene-pyrrolinones with a conjugation chain extended by vinylene and phenylene-vinylene groups were studied: five of them were synthesized for the first time. Their structures were estimated theoretically by density functional theory (DFT) and proved by X-ray diffraction techniques in two cases. Structural changes upon Z/E photoisomerization in solution were studied by a combination of H-1 NMR spectroscopy and DFT CIAO method. Both types of conjugation extension caused a bathochromic shift in absorption. Vinylene extension produced the compounds fluorescent in solution. N-methylated derivatives have shown solid-state fluorescence. DIKETOPYRROLOPYRROLE DPP PIGMENTS; DIKETO-PYRROLO-PYRROLES; X-RAY; DIFFRACTION; NITRILES; ESTERS; STATE ; Photoisomerization; Conjugation; X-ray diffraction techniques; Density functional theory; NMR spectroscopy

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