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Synthesis and self-aggregation of chlorophyll derivatives possessing a pyrazole ring at the C3 position

Paper ID Volume ID Publish Year Pages File Format Full-Text
26462 43954 2015 9 PDF Available
Title
Synthesis and self-aggregation of chlorophyll derivatives possessing a pyrazole ring at the C3 position
Abstract

•The β-diketonate group connected with chlorin was reacted with hydrazines.•C3-Pyrazolylated or pyrazolinylated chlorophyll derivatives were synthesized.•The substituents on the heterocyclic ring affected the optical properties of chlorin.•N-Unsubstituted pyrazole–zinc chlorin dimerized in nonpolar organic solvent.

Chlorophyll compounds possessing an N-(un)substituted pyrazole ring at the C3 position were synthesized by the reaction of chlorophyll-a derivative having a trifluoromethyl-β-diketonate group with (substituted) hydrazines in 2,2,2-trifluoroethanol through the pyrazoline ring. The substituents on the C3-heterocyclic 5-membered ring affected the electronic absorption and emission of the monomeric chlorin molecules. Vis, CD and 1H NMR spectra of the zinc chlorin bearing an N-unsubstituted pyrazole showed its dimerization in a nonpolar organic solvent.

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Keywords
Diketonate; Fluorescence emission; Hydrazine; Methyl pyropheophorbide; UV–vis absorption
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Synthesis and self-aggregation of chlorophyll derivatives possessing a pyrazole ring at the C3 position
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 313, 1 December 2015, Pages 27–35
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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