The synthesis,absorption and fluorescence of polar diketo-pyrrolo-pyrroles |
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| Authors: | Stanislav Luňák Jan Vyňuchal Martin Vala Lukáš Havel Radim Hrdina |
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| Affiliation: | 1. Department of Organic Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 95, CZ-532 10 Pardubice, Czech Republic;2. Research Institute of Organic Syntheses, Rybitví 296, CZ-533 54, Rybitví, Czech Republic;3. Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech Republic;1. Babes-Bolyai University, Department of Chemistry, 11 Arany János St., 400028 Cluj-Napoca, Romania;2. Babes-Bolyai University, Department of Chemical Engineering, 11 Arany János St., 400028 Cluj-Napoca, Romania;3. National Institute for Research and Development of Isotopic and Molecular Technologies, Molecular and Biomolecular Physics Department, 65-103, Donath St., PO Box 700, 400293 Cluj-Napoca 5, Romania;4. University of Reims Champagne-Ardenne, ICMR, UMR 7312, BP 1039, 51687 Reims, France;5. University of Strasbourg, Faculty of Pharmacy, 74, route du Rhin, BP 60024, 67401 Illkirch cedex, France;1. State Key Laboratory of Chemical Engineering and School of Chemical Engineering, East China University of Science and Technology, Shanghai, 200237, China;2. Key Laboratory for Advanced Materials, Institute of Fine Chemical, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China;1. Institut de Chimie Moléculaire de l''Université de Bourgogne, UMR 6302, CNRS, Univ. Bourgogne Franche-Comté, 9, Avenue Alain Savary, BP 47870, 21078, Dijon cedex, France;2. Institut Universitaire de France, 1, Rue Descartes, Bâtiment MONGE, 75005, Paris, France |
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| Abstract: | The effect of electron-donor (piperidino) and electron-acceptor (cyano) groups on the absorption maxima of some diketo-pyrrolo-pyrroles in DMSO solution was investigated both experimentally and theoretically. The syntheses of push–pull substituted 3-(4-piperidinophenyl)-6-(4-cyanophenyl)-2,5-dihydropyrrolo3,4-c]pyrrol-1,4-dione are reported for the first time; 3,6-diphenyl-2,5-dihydropyrrolo3,4-c]pyrrol-1,4-diones substituted with either one or two piperidino or cyano groups in the para-positions of the phenyl rings were also synthesized. Whilst both types of substituent produce a bathochromic and hyperchromic shifts with respect to the parent unsubstituted compound, the influence of the piperidino group is strongest. Symmetrically substituted derivatives show well-resolved vibronic structures, while the spectra of polar, unsymmetrical compounds were poorly resolved because of strong dipole–dipole interaction with the polar solvent. The fluorescence of all compounds was intense and a significant increase in the Stokes shift of polar derivatives was another consequence of dipole–dipole interactions with the solvent in the excited state. |
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