On the cleavage process of the N-trifluoromethylsulfonyloxy-1,8-naphthalimide photoacid generator

被引:36
作者
Malval, Jean-Pierre
Morlet-Savary, Fabrice
Allonas, Xavier
Fouassier, Jean-Pierre
Suzuki, Shota
Takahara, Shigeru
Yamaoka, Tsuguo
机构
[1] Univ Haute Alsace, CNRS, UMR 7525, Dept Photochem, F-68093 Mulhouse, France
[2] Chiba Univ, Fac Engn, Dept Informat & Image Sci, Chiba 2638522, Japan
关键词
D O I
10.1016/j.cplett.2007.06.082
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 photocleavage mechanism of N-tritluoromethylsulfonyloxy-1,8-naphthalimide usable as a photoacid generator is reported. Stationary fluorescence measurements, picosecond transient spectroscopy, infrared analysis and DFT calculations support a homolytic N-O bond cleavage followed by an internal cyclic rearrangement of the 1,8 naphthalimide core which lead to benz[cd]indol-2(1H)-one, carbon dioxide and sulfonic acid. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:323 / 327
页数:5
相关论文
共 12 条
[1]   Evidence of homolytic and heterolytic pathways in the photodissociation of iminosulfonates and direct detection of the p-toluenesulfonyloxyl radical [J].
Pamela A. Arnold ;
Lauren E. Fratesi ;
Elena Bejan ;
Jim Cameron ;
Gerd Pohlers ;
H. Liu ;
J. C. Scaiano .
Photochemical & Photobiological Sciences, 2004, 3 (9) :864-869
[2]   Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation [J].
Demeter, A ;
Berces, T ;
Biczok, L ;
Wintgens, V ;
Valat, P ;
Kossanyi, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (06) :2001-2011
[3]  
Fouassier JP., 1993, RAD CURING POLYM SCI
[4]  
FRISCH MJ, 2001, GAUSSIAN 98 REVISION
[5]   1,8-naphthalimides as stereochemical probes for chiral amines:: A study of electronic transitions and exciton coupling [J].
Gawronski, J ;
Gawronska, K ;
Skowronek, P ;
Holmén, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :234-241
[6]   SUCCINIMIDYL AND PHTHALIMIDYL RADICALS - MATRIX-ISOLATION ESR STUDY [J].
KASAI, PH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :2875-2880
[7]   1,8-naphthalimides in phosphorescent organic LEDs: The interplay between dopant, exciplex, and host emission [J].
Kolosov, D ;
Adamovich, V ;
Djurovich, P ;
Thompson, ME ;
Adachi, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9945-9954
[9]   Photophysics of a bridged 7-diethylamino-4-methyl-coumarin C102: Studying the hydrogen bonding effect by time resolved stimulated emission [J].
Morlet-Savary, F ;
Ley, C ;
Jacques, P ;
Fouassier, JP .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (49) :11026-11033
[10]   Mechanism of reaction and photoacid generation of N-oxysuccinimidoarylsulfonate PAGs:: A laser flash photolytic study [J].
Ortica, F ;
Coenjarts, C ;
Scaiano, JC ;
Liu, H ;
Pohlers, G ;
Cameron, JF .
CHEMISTRY OF MATERIALS, 2001, 13 (07) :2297-2304