Synthesis and Evaluation of a Photochromic Surfactant for Organic Reactions in Aqueous Media

被引:36
作者
Drillaud, Nicolas [1 ]
Banaszak-Leonard, Estelle [1 ]
Pezron, Isabelle [1 ]
Len, Christophe [1 ]
机构
[1] Univ Technol Compiegne, EA UTC ESCOM 4297, Ctr Rech Royallieu, F-60205 Compiegne, France
关键词
ACYLATION; AMINES; WATER; TELOMERIZATION; BUTADIENE; REARRANGEMENT; CLEAVAGE; KETONES; SYSTEM; MILD;
D O I
10.1021/jo301466w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel photochromic azobenzene-based surfactant was described for organic chemistry in water. The molecule 4-butylazobenzyl-4'-triazologlucuronic acid sodium salt thus synthesized can be isomerized from its trans to its cis form reversibly in solution by simple light irradiation. That property allowed the recyclability of a model acetylation reaction performed in the surfactant media, compared to the well-known, commercially available sodium dodecyl sulfate surfactant media.
引用
收藏
页码:9553 / 9561
页数:9
相关论文
共 44 条
[11]   UV-Induced Bursting of Cell-Sized Multicomponent Lipid Vesicles in a Photosensitive Surfactant Solution [J].
Diguet, Antoine ;
Yanagisawa, Miho ;
Liu, Yan-Jun ;
Brun, Elodie ;
Abadie, Sacha ;
Rudiuk, Sergii ;
Baigl, Damien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) :4898-4904
[12]   Reactions in micellar systems [J].
Dwars, T ;
Paetzold, E ;
Oehme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7174-7199
[13]   Synthesis and characterization of new 1,4 and 1,5-disubstituted glucopyranosyl 1,2,3-triazole by 1,3-dipolar cycloaddition [J].
El Moncef, Abdelkarim ;
El Hadrami, El Mestafa ;
Ben-Tama, Abdeslem ;
Ramirez de Arellano, Carmen ;
Zaballos-Garcia, Elena ;
Stiriba, Salah-Eddine .
JOURNAL OF MOLECULAR STRUCTURE, 2009, 929 (1-3) :6-9
[14]   Effect of hydrophilic group on thin film formation using redox-active surfactants with an azobenzene group [J].
Fujita, Haruko ;
Shrestha, Nabeen K. ;
Ogihara, Hitoshi ;
Saji, Tetsuo .
ELECTROCHIMICA ACTA, 2008, 53 (28) :8161-8165
[15]   Carboxamides combining favorable olfactory properties with insect repellency [J].
Gaudin, Jean-Marc ;
Lander, Thierry ;
Nikolaenko, Olga .
CHEMISTRY & BIODIVERSITY, 2008, 5 (04) :617-635
[16]   Azobenzenes-synthesis and carbohydrate applications [J].
Hamon, Florian ;
Djedaini-Pilard, Florence ;
Barbot, Francis ;
Len, Christophe .
TETRAHEDRON, 2009, 65 (49) :10105-10123
[17]   The growing impact of click chemistry on drug discovery [J].
Kolb, HC ;
Sharpless, KB .
DRUG DISCOVERY TODAY, 2003, 8 (24) :1128-1137
[18]   Surface activity and micelle formation of anionic azobenzene-linked surfactants [J].
Kozlecki, T ;
Sokolowski, A ;
Wilk, KA .
LANGMUIR, 1997, 13 (26) :6889-6895
[19]   Manganese-Catalyzed Cleavage of a Carbon-Carbon Single Bond between Carbonyl Carbon and α-Carbon Atoms of Ketones [J].
Kuninobu, Yoichiro ;
Uesugi, Tadamasa ;
Kawata, Atsushi ;
Takai, Kazuhiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) :10406-10408
[20]   Synthesis of amphiphilic phenylazophenyl glycosides and a study of their liquid crystal properties [J].
Laurent, N ;
Lafont, D ;
Dumoulin, F ;
Boullanger, P ;
Mackenzie, G ;
Kouwer, PHJ ;
Goodby, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15499-15506