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Photodimerized 7-hydroxycoumarin with improved solubility in PMMA: Single-photon and two-photon-induced photocleavage in solution and PMMA films

Paper ID Volume ID Publish Year Pages File Format Full-Text
28231 44066 2007 5 PDF Available
Title
Photodimerized 7-hydroxycoumarin with improved solubility in PMMA: Single-photon and two-photon-induced photocleavage in solution and PMMA films
Abstract

tert-Butyldimethylsilyl-chloride (TBS) revealed to be a photostable protecting group for the photodimerization of 7-hydroxycoumarin in a [2 + 2]-cycloaddition. TBS-functionalized coumarin dimers show an about 100-fold increased solubility in organic solvents enabling them to be easily incorporated into polymeric films, e.g., PMMA. In the described photochemical dimerization reaction almost pure anti-head-to-head isomer is obtained. The single- and two-photon absorption-induced cycloreversion reactions in acetonitrile as well as in PMMA matrix were investigated and the two-photon absorption cross sections and quantum yields were determined to be around 1 GM and about 0.36, respectively. The only product obtained upon photocleavage of the dimer is the TBS-protected 7-hydroxycoumarin monomer. The TBS-protecting group withstands the high light intensities required for two-photon absorption-induced photocleavage without any noticeable degradation. The mild deprotection conditions for tert-butyldimethylsilyl-ethers (TBS-ethers), the chemical stability of the compound as well as its significantly improved solubility in organic solvents and its miscibility with acrylic polymers, make this a very useful compound for potential applications in 3D volumetric optical data storage and photocontrolled drug delivery.

Keywords
7-Hydroxycoumarin; Coumarin dimer; Photodimerization; Two-photon absorption; Solubility; tert-Butyldimethylsilyl-ether
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Photodimerized 7-hydroxycoumarin with improved solubility in PMMA: Single-photon and two-photon-induced photocleavage in solution and PMMA films
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 187, Issues 2–3, 15 April 2007, Pages 242–246
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us