MetaCentrum Yearbook 2010

0367291 - ÚMCH 2012 RIV CZ eng M - Monography Chapter
Toman, Petr - Weiter, M. - Vala, M.
Quantum chemical study of soluble diphenyl-diketo-pyrrolopyrrole derivatives.
MetaCentrum Yearbook 2010. Příbram: CESNET, 2011 - (Křenková, I.; Hanousek, P.; Matyska, L.), s. 75-81. ISBN 978-80-904689-3-1
R&D Projects: GA ČR(CZ) GAP205/10/2280; GA MŠMT MEB051010
Institutional research plan: CEZ:AV0Z40500505
Keywords : diphenyl-diketo-pyrrolopyrrole * quantum chemical calculation * molecular conformation
Subject RIV: BM - Solid Matter Physics ; Magnetism
https://www.metacentrum.cz/export/sites/metacentrum/cs/about/results/yearbooks/Rocenka2010_web.pdf

Newly synthesized diphenyl-diketo-pyrrolopyrroles possessing electron-donating or withdrawing groups were characterized by means of quantum chemical methods. Some of these derivatives were N-alkylated on the central unit in order to increase their solubility. It was found that the most important parameter governing absorption and luminescence is the effective extent of the conjugation, which is deeply wedded with the planarity of the molecular conformation. Unlike N-alkylation leading to significant phenyl ring turns, substitution of either electron-donating or withdrawing groups breaks the molecule planarity only slightly. The main effect of the substitution of electron-donating groups is a hyperchromic and bathochromic shift in absorption spectra. This finding suggests electron-accepting character of the central unit. However, it should be noted that N-alkylation reduces this effect.
Permanent Link: http://hdl.handle.net/11104/0202027