Photochemistry of 4-Chlorophenol and 4-Chloroanisole Adsorbed on MFI Zeolites: Supramolecular Control of Chemoselectivity and Reactive Intermediate Dynamics

被引：10

作者：

Da Silva, Jose P. ^{[1
]}

Jockusch, Steffen ^{[2
]}

Martinho, Jose M. G. ^{[3
]}

Ottaviani, M. Francesca ^{[4
]}

Turro, Nicholas J. ^{[2
]}

机构：

[1] Univ Algarve, Fac Ciencias & Tecnol, P-8005139 Faro, Portugal

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

[3] Inst Super Tecn, Ctr Quim Fis Mol, P-1049001 Lisbon, Portugal

[4] Univ Urbino, Dept Geol Sci Chem & Environm Technol, I-61029 Urbino, Italy

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

基金：

美国国家科学基金会;

关键词：

RADICAL CATIONS; PHOTOLYSIS; SPECTRA;

D O I：

10.1021/ol1010906

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The phototransformation of aryl chlorides adsorbed on MFI zeolites is markedly different from that observed in solution and other solid surfaces such as silica. The formation of radical cations and the constraints imposed by the channels shift the reactivity from the C-CI bond to the O-R bond. Irradiation generates kinetically stabilized intermediates that can be characterized using conventional steady-state spectroscopic techniques, and these intermediates can be used as ordinary chemical reagents.

引用

页码：3062 / 3065

页数：4

共 20 条

[1] BREEKER DW, 1974, ZEOLITE MOL SIEVES S
[2] ACID ZEOLITES AS ELECTRON ACCEPTORS - USE OF THIANTHRENE RADICAL-CATION AS A PROBE
CORMA, A
FORNES, V
GARCIA, H
MARTI, V
MIRANDA, MA
[J]. CHEMISTRY OF MATERIALS, 1995, 7 (11) : 2136 - 2143
[3] Surface photochemistry of pesticides containing 4-chlorophenoxyl chromophore
Da Silva, Jose P.
Vieira Ferreira, Luis F.
Osipov, Ivan
Machado, Isabel Ferreira
[J]. JOURNAL OF HAZARDOUS MATERIALS, 2010, 179 (1-3) : 187 - 191
[4] Probing the photoreactivity of aryl chlorides with oxygen
Da Silva, Jose P.
Jockusch, Steffen
Turro, Nicholas J.
[J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2009, 8 (02) : 210 - 216
[5] Photochemistry of 4-chlorophenol on cellulose and silica
Da Silva, JP
Ferreira, LFV
Da Silva, AM
Oliveira, AS
[J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2003, 37 (20) : 4798 - 4803
[6] A comparative study of the photophysics and photochemistry of 4-chlorophenol adsorbed on silicalite and β-cyclodextrin
Da Silva, JP
Ferreira, LFV
Da Silva, AM
Oliveira, AS
[J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2002, 151 (1-3) : 157 - 164
[7] SUBSTITUENT EFFECTS IN ESR-SPECTRA OF PHENOXYL RADICALS
DIXON, WT
MOGHIMI, M
MURPHY, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS II, 1974, 70 (10): : 1713 - 1720
[8] Generation and reactions of organic radical cations in zeolites
García, H
Roth, HD
[J]. CHEMICAL REVIEWS, 2002, 102 (11) : 3947 - 4007
[9] FORMATION AND REACTIVITY OF 4-OXOCYCLOHEXA-2,5-DIENYLIDENE IN THE PHOTOLYSIS OF 4-CHLOROPHENOL IN AQUEOUS-SOLUTION AT AMBIENT-TEMPERATURE
GRABNER, G
RICHARD, C
KOHLER, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) : 11470 - 11480
[10] Supramolecular steric effects as the means of making reactive carbon radicals persistent. Quantitative characterization of the external surface of MFI zeolites through a persistent radical probe and a langmuir adsorption isotherm
Hirano, T
Li, W
Abrams, L
Krusic, PJ
Ottaviani, MF
Turro, NJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1319 - 1330

← 1 2 →