Influence of chiral ionic liquids on the excited-state properties of naproxen analogs

被引：13

作者：

Adhikary, Ramkrishna ^{[1
]}

Bose, Sayantan ^{[1
]}

Mukherjee, Prasun ^{[1
]}

Thite, Aniket ^{[1
]}

Kraus, George A. ^{[1
]}

Wijeratne, Aruna B. ^{[2
]}

Sharma, Pritesh S. ^{[2
]}

Armstrong, Daniel W. ^{[2
]}

Petrich, Jacob W. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

JOURNAL OF PHYSICAL CHEMISTRY B | 2008年 / 112卷 / 25期

关键词：

D O I：

10.1021/jp711508b

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The synthesis and decolorization of chiral room-temperature ionic liquids based upon 1-methyl imidazole and chloromethyl menthyl ether is reported. The excellent optical quality of these solvents permits the investigation of the effects of the two enantiomers on the excited-state photophysics of (S)-N-methyl-2-pyrrolidinemethyl 2(S)-(6-methoxy-2-naphthyl)propionate [(S,S)-NPX-PYR]. Whereas in conventional bulk polar solvents such as acetonitrile, (S,S)-NPX-PYR is known to execute excited-state intramolecular electron transfer and to form exciplexes, in these chiral solvents these nonradiative processes are absent. The chiral solvents do, however, induce a small but reproducible (similar to 10%) stereodifferentiation in the fluorescence lifetime of (S,S)-NPX-PYR as well as in the parent compound, (S)-naproxen. To our knowledge, this is the first example of chiral ionic liquids inducing such an effect on photophysical properties.

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收藏

页码：7555 / 7559

页数：5

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共 40 条

[21] Moisture stable dialkylimidazolium salts as heterogeneous and homogeneous Lewis acids in the Diels-Alder reaction [J].

Howarth, J ;

Hanlon, K ;

Fayne, D ;

McCormac, P .

TETRAHEDRON LETTERS, 1997, 38 (17) :3097-3100

[22] Stereoselectivity in the triplet decay of chiral benzophenone-naphthalene bichromophoric systems [J].

Jiménez, MC ;

Stiriba, SE ;

Tormos, R ;

Pérez-Prieto, J ;

Miranda, MA .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2004, 3 (01) :36-38

[23] Intramolecular electron transfer within a covalent, fixed-distance donor-acceptor molecule in an ionic liquid [J].

Lockard, Jenny V. ;

Wasielewski, Michael R. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (40) :11638-11641

[24] Photoinduced electron transfer in ionic liquids:: Use of 2,4,6-triphenylthiapyrylium as a photosensitizer probe [J].

Marquis, Severine ;

Ferrer, Belen ;

Alvaro, Mercedes ;

Garcia, Hermenegildo ;

Roth, Heinz D. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (30) :14956-14960

[25] Regio- and stereo-selectivity in the intramolecular quenching of the excited benzoylthiophene chromophore by tryptophan [J].

Miranda, MA ;

Lahoz, A ;

Boscá, F ;

Metni, MR ;

Abdelouahab, FB ;

Castell, JV ;

Pérez-Prieto, J .

CHEMICAL COMMUNICATIONS, 2000, (22) :2257-2258

[26] Enantioselective discrimination in the intramolecular quenching of an excited aromatic ketone by a ground-state phenol [J].

Miranda, MA ;

Lahoz, A ;

Martínez-Máñez, R ;

Boscá, F ;

Castell, JV ;

Pérez-Prieto, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11569-11570

[27] Dynamic solvation in phosphonium ionic liquids:: Comparison of bulk and micellar systems and considerations for the construction of the solvation correlation function, C(t) [J].

Mukherjee, Prasun ;

Crank, Jeffrey A. ;

Sharma, Pritesh S. ;

Wijeratne, Artma B. ;

Adhikary, Ramkrishna ;

Bose, Sayantan ;

Armstrong, Daniel W. ;

Petrich, Jacob W. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (11) :3390-3396

[28] How transparent are the imidazolium ionic liquids?: A case study with 1-methyl-3-butylimidazolium hexafluorophosphate, [bmim][PF6] [J].

Paul, A ;

Mandal, PK ;

Samanta, A .

CHEMICAL PHYSICS LETTERS, 2005, 402 (4-6) :375-379

[29] Photoinduced electron transfer reaction in room temperature ionic liquids: A combined laser flash photolysis and fluorescence study [J].

Paul, Aniruddha ;

Samanta, Anunay .

JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (08) :1957-1962

[30] Stereoselective fluorescence quenching by photoinduced electron transfer in naphthalene-amine dyads [J].

Pischel, U ;

Abad, S ;

Miranda, MA .

CHEMICAL COMMUNICATIONS, 2003, (09) :1088-1089

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