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The synthesis of bi- and trichromophoric dyes bearing an s-triazinyl ring spacer
Authors:Numan Almonasy  Milo? Nepra?  ?árka Hyková  Antonin Ly?ka  Ji?i ?ermák  Miroslav Dvo?ák  Martin Michl
Affiliation:1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 95, CZ-532 10 Pardubice, Czech Republic;2. Research Institute for Organic Syntheses (VUOS), Rybitví 296, CZ-533 54 Pardubice, Czech Republic;3. Department of Physical Electronics, Faculty of Nuclear Sciences and Physical Engineering, Czech Technical University in Prague, V Hole?ovi?kách 2, CZ-180 00 Prague, Czech Republic;1. Department of Chemistry, University of Delhi, Delhi 110007, India;2. Center for Advanced Materials, University of Massachusetts Lowell, Lowell, MA 01854, USA;3. Indian Institute of Science Education and Research Pune, Pune, Maharashtra 411008, India;4. US Army Natick Soldier Research, Development and Engineering Center, Natick, MA 01760, USA;1. Key Laboratory of Chemo/Biosensing and Detection, School of Chemistry and Chemical Engineering, Xuchang University, Xuchang, 461000, PR China;2. Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, PR China;1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea;2. Interdisciplinary School of Green Energy, Ulsan National Institute of Science and Technology, Ulsan 689-798, Republic of Korea;3. Department of Industrial Chemistry, Pukyong National University, Busan 608-739, Republic of Korea;4. The WCU Center for Synthetic Polymer Bioconjugate Hybrid Materials, Department of polymer Science and Engineering, Pusan National University, Busan 609-735, Republic of Korea;1. Departamento de Física, Universidade Federal de Santa Catarina?UFSC, 88040-900 Florianópolis, SC, Brazil;2. Departamento de Física, Universidade Federal de Ouro Preto – UFOP, 35400-000 Ouro Preto, MG, Brazil;3. Department of Electronic Materials, Institute of Materials Science, Technical University of Darmstadt, Alarich-Weiss Strasse 2, D-64287 Darmstadt, Germany;4. Centre de Recherche Paul Pascal, Université de Bordeaux & CNRS, 115 Avenue Schweitzer, 33600 Pessac, France
Abstract:An alternative procedure has been described for the syntheses of several bi- and trichromophoric compounds consisting of 1-aminopyrene and 3-aminobenzanthrone chromophoric subsystems connected by an s-triazinyl ring spacer. The synthetic method used, which utilises an autoclave under autogenous pressure, is suitable for the nucleophilic substitution of both chlorine atoms within the triazinyl ring by weakly basic aromatic amines. The structures of the synthesized compounds were confirmed using elemental analysis, 1H NMR, and mass spectra. UV/vis absorption and fluorescence spectra and fluorescence quantum yields were measured. The dependence of fluorescence intensity and fluorescence quantum yields on solvent polarity was investigated.
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