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1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability

Paper ID Volume ID Publish Year Pages File Format Full-Text
27151 44005 2010 7 PDF Available
Title
1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability
Abstract

Coumarins are well known for reversible dimer formation with wavelengths greater than 300 nm and dimer cleavage below 300 nm. In a photochemical [2+2]-cycloaddition a cyclobutane ring is formed. Formation as well as cleavage of the cyclobutane ring may be accomplished by a single-photon-absorption as well as by a two-photon-absorption triggered reaction. The coumarin system is of interest for various kinds of applications, ranging from drug delivery for ophthalmic implants to optical data storage. However, the two-photon-absorption coefficient of coumarin dimers is rather low falling in the range of 1 GM in the visible range. We present here a substitute for the coumarin dimer system which not only has an about one order of magnitude higher two-photon-absorption coefficient, but also overcomes several other problems of the coumarin dimer system. Coumarines and in particular coumarine dimers have a very limited solubility in common solvents and are susceptible to hydrolysis of the lactone ring, which leads to an undesired complexity in the photochemical cleavage reaction. The 1,1-dimethylnaphtalenone dimers introduced here show excellent stability, lead only to a single cleavage product, and have a two-photon-absorption coefficient of about 10 GM at 532 nm. These properties make the 1,1-dimethylnaphtalenone dimers a superior substitute over the well-known coumarin dimers in particular in applications where two-photon-absorption induced photocleavage is required.

Keywords
Two-photon-absorption; Coumarin dimers; Asymmetric cleavage; Lactone ring; Dimethylnaphthalenone
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1,1-Dimethylnaphthalenon-dimers as photocleavable linkers with improved two-photon-absorption efficiency and hydrolytic stability
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 209, Issues 2–3, 25 January 2010, Pages 128–134
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
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