Excited-state dynamics of spiropyran-derived merocyanine isomers

被引:75
作者
Wohl, CJ [1 ]
Kuciauskas, D [1 ]
机构
[1] Virginia Commonwealth Univ, Dept Chem, Richmond, VA 23284 USA
关键词
D O I
10.1021/jp053782x
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
Merocyanine (MC) isomers that are formed after absorption of a UV photon by 1',3'-dihydro- 1',3'-3'-trimethyl-6-nitrospiro[2H-1-benzopyran-2',2'-(2H)-indole] were studied. Several, predominantly TTC and TTT, merocyanine isomers are present in toluene solution ("T" and "C" indicate trans and cis conformations of the C-C bonds in the methine bridge). Excitation in the MC visible absorption band (at 490, 550, and 630 nm) with 100 A laser pulses was used to study MC excited-state dynamics. Internal conversion on the picosecond time scale was found to be the dominant relaxation pathway. Excited-state isomerization reactions were also observed. Excitation at 630 nm (assigned to TTC isomer excitation) leads to formation of a third isomer (either CTC or CTT). Excitation at 490 nm (assigned to TTT isomer excitation) leads to more complex excited-state relaxation, including formation of two isomers: TTC (absorption at 600 nm) and CTC or CTT (absorption at 650 nm).
引用
收藏
页码:22186 / 22191
页数:6
相关论文
共 32 条
[1]   Spiropyrans and spirooxazines for memories and switches [J].
Berkovic, G ;
Krongauz, V ;
Weiss, V .
CHEMICAL REVIEWS, 2000, 100 (05) :1741-1753
[2]   Ground- and first-excited-singlet-state electric dipole moments of some photochromic spirobenzopyrans in their spiropyran and merocyanine form [J].
Bletz, M ;
Pfeifer-Fukumura, U ;
Kolb, U ;
Baumann, W .
JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (10) :2232-2236
[3]   Conical intersection mechanism for photochemical ring opening in benzospiropyran compounds [J].
Celani, P ;
Bernardi, F ;
Olivucci, M ;
Robb, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10815-10820
[4]   Photoprocesses in spiropyran-derived merocyanines [J].
Chibisov, AK ;
Gorner, H .
JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (24) :4305-4312
[5]   Photochromism of spirobenzopyranindolines and spironaphthopyranindolines [J].
Chibisov, AK ;
Görner, H .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (03) :424-431
[6]   Theoretical study of spiropyran-merocyanine thermal isomerization [J].
Cottone, G ;
Noto, R ;
La Manna, G .
CHEMICAL PHYSICS LETTERS, 2004, 388 (1-3) :218-222
[7]   PHOTOCHEMICAL RING-OPENING REACTION OF INDOLINOSPIROPYRANS STUDIED BY SUBPICOSECOND TRANSIENT ABSORPTION [J].
ERNSTING, NP ;
ARTHENENGELAND, T .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (14) :5502-5509
[8]   The role of large conformational changes in efficient ultrafast internal conversion: Deviations from the energy gap law [J].
Fidder, H ;
Rini, M ;
Nibbering, ETJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3789-3794
[9]   Conformations of nitro-substituted spiropyran and merocyanine studied by low-temperature matrix-isolation infrared spectroscopy and density-functional-theory calculation [J].
Futami, Y ;
Chin, MLS ;
Kudoh, S ;
Takayanagi, M ;
Nakata, M .
CHEMICAL PHYSICS LETTERS, 2003, 370 (3-4) :460-468
[10]   Photochromism of nitrospiropyrans:: effects of structure, solvent and temperature [J].
Görner, H .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (03) :416-423