Carbanion-mediated photocages: Rapid and efficient photorelease with aqueous compatibility

被引:59
作者
Lukeman, M [1 ]
Scaiano, JC [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ja0517062
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new photocage is proposed, based on ketoprofen-derived compounds and mediated by carbanions. The new photocage has significant advantages over the widely used o-nitrobenzyl derivatives, including aqueous compatibility, faster photorelease, higher quantum yield, and innocuous byproducts. The photorelease of ibuprofen illustrates the properties of the new photocage. Copyright © 2005 American Chemical Society.
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页码:7698 / 7699
页数:2
相关论文
共 15 条
[1]  
Boscá F, 2001, PHOTOCHEM PHOTOBIOL, V74, P637, DOI 10.1562/0031-8655(2001)074<0637:POTNAI>2.0.CO
[2]  
2
[3]   Photolytic cleavage of 1-(2-nitrophenyl)ethyl ethers involves two parallel pathways and product release is rate-limited by decomposition of a common hemiacetal intermediate [J].
Corrie, JET ;
Barth, A ;
Munasinghe, VRN ;
Trentham, DR ;
Hutter, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (28) :8546-8554
[4]   Absolute rate constants for water protonation of 1-(3-benzoylphenyl)alkyl carbanions [J].
Cosa, G ;
Llauger, L ;
Scaiano, JC ;
Miranda, MA .
ORGANIC LETTERS, 2002, 4 (18) :3083-3085
[5]   Influence of solvent polarity and base concentration on the photochemistry of ketoprofen:: independent singlet and triplet pathways [J].
Cosa, G ;
Martínez, LJ ;
Scaiano, JC .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1999, 1 (15) :3533-3537
[6]   The N-(2-acetoxyethyl) group as a new photolabile protecting group [J].
Cossy, J ;
Rakotoarisoa, H .
TETRAHEDRON LETTERS, 2000, 41 (13) :2097-2099
[7]  
Givens R.S., 2004, CRC HDB PHOTOCHEMIST
[8]   Photochemical reaction mechanisms of 2-nitrobenzyl compounds:: Methyl ethers and caged ATP [J].
Il'ichev, YV ;
Schwörer, MA ;
Wirz, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4581-4595
[9]   First determination of absolute rate constants for the reaction of aroyl-substituted benzyl carbanions in water and DMSO [J].
Llauger, L ;
Cosa, G ;
Scaiano, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15308-15312
[10]   Transient intermediates in the laser flash photolysis of ketoprofen in aqueous solutions: Unusual photochemistry for the benzophenone chromophore [J].
Martinez, LJ ;
Scaiano, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (45) :11066-11070