Synthesis of functionalized core-modified sapphyrins and covalently linked porphyrin-sapphyrin dyads
DSpace at IIT Bombay
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Title |
Synthesis of functionalized core-modified sapphyrins and covalently linked porphyrin-sapphyrin dyads
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Creator |
MALAKALAPALLI, RR
MANGALAMPALLI, R |
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Subject |
Core-modified porphyrins
Thiasapphyrin building blocks Anion sensor NONLINEAR-OPTICAL PROPERTIES MODIFIED EXPANDED PORPHYRINS MESO-ARYL SAPPHYRINS ANION-BINDING ENERGY-TRANSFER AROMATICITY HETEROATOMS PENTAPHYRIN COMPLEXES DYNAMICS |
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Description |
We adopted simple synthetic strategy to synthesize mono-functionalized thiasapphyrins containing functionalized aryl group in the meso-position at thiophene side. The thiasapphyrin building block containing iodophenyl functional group was coupled with three different porphyrin building blocks with N-4. N3S and N2S2 cores containing meso-ethynylphenyl functional group under mild Pd(0) coupling conditions to synthesize three covalently linked diphenyl ethyne bridged porphyrin-thiasapphyrin dyads. The porphyrin thiasapphyrin dyads were characterized by mass, NMR, absorption, electrochemical and fluorescence techniques. The NMR, absorption and electrochemical studies indicated that the two components in dyads interact weakly and retain their individual identities. The steady state fluorescence studies indicated that the porphyrin fluorescence is reduced to a significant extent because of energy and/or electron transfer to the thiasapphyrin unit. The protonation studies indicated that N-4 porphyrin unit is more basic, whereas N3S and N2S2 porphyrin units are less basic compared to thiasapphyrin unit in respective dyads. We explored the potential of dyads as fluorescent anion sensors and showed that two out of three dyads can be used as fluorescent anion sensors. (C) 2011 Elsevier Ltd. All rights reserved.
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Publisher |
PERGAMON-ELSEVIER SCIENCE LTD
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Date |
2014-10-15T16:58:14Z
2014-10-15T16:58:14Z 2012 |
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Type |
Article
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Identifier |
TETRAHEDRON, 68(4)1306-1314
http://dx.doi.org/10.1016/j.tet.2011.11.030 http://dspace.library.iitb.ac.in/jspui/handle/100/15269 |
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Language |
en
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