Patent DE-102011109254-A1 (DE)
Title: Use of a benzoperylene tetracarboxylic acid imide anhydride compound, a benzoperylene tetracarboxylic acid imide compound and a benzoperylene derivative e.g. as triplet sensitizers, and to generate singlet oxygen for Diels-Alder reactions
Inventor: LANGHALS HEINZ
IPC: C01B13/00
Filed: 2011-08-01
Abstract: Use of a perylene compound (Q) comprising a benzoperylene tetracarboxylic acid imide anhydride compound (I), a benzoperylene tetracarboxylic acid imide compound (II) and a benzoperylene derivative (III) as triplet sensitizers and for generating singlet oxygen is claimed. Use of a perylene compound (Q) comprising a benzoperylene tetracarboxylic acid imide anhydride compound of formula (I), a benzoperylene tetracarboxylic acid imide compound of formula (II) and a benzoperylene derivative of formula (III) as triplet sensitizers and for generating singlet oxygen is claimed. R1-R9 : H or linear 1-37C-alkyl, in which 1-10 CH 2unit(s) is optionally replaced by carbonyl, O, S, Se, Te, cis- or trans-CH=CH-, in which CH unit is optionally replaced by N, CC, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene, in which one or two CH groups are optionally replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10 - or 9,10-disubstituted anthracene, in which one or two CH groups are optionally replaced by N, up to 12 individual H of CH 2groups are optionally replaced by F, Cl, Br, I or CN or linear up to 18C-alkyl, where 1-6 CH 2-units are optionally replaced by carbonyl, O, S, Se, Te, cis- or trans-CH=CH-groups, where one CH-unit is optionally be replaced by N, CC, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene, where one or two C are optionally replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene, where one or two C are optionally replaced by N, up to 12 individual H of the CH 2groups of the alkyl are replaced by F, Cl, Br, I, CN or linear up to 18C-alkyl, in which 1-6 CH 2-units are optionally replaced by carbonyl, O, S, Se, Te, cis- or trans CH=CH-, where one CH-unit is optionally replaced by N, CC, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3, 4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene, in which one or two C are replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene, in which 1 or 2 C atoms are replaced by N, where, instead of being able to carry substituents, the free valences of the methine or quaternary carbon atoms are associated in pairs to form rings, such as cyclohexane and R1-R9 are optionally contains F, Cl, Br or I; X : 1-12 CH 2-units, which are replaced by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which one CH unit is optionally replaced by N, CC, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2, 5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene, in which 1 or 2 CH groups are optionally replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene, in which 1 or 2 CH groups are optionally replaced by N, up to 12 single H of the CH 2are optionally replaced by F, Cl, Br, I, CN or linear up to 18C-alkyl, in which 1-6 CH 2-units are replaced by carbonyl, O, S, Se, Te, cis or trans-CH=CH-, in which on CH unit is replaced by N, CC, 1,2, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2.6- or 2,7- disubstituted naphthalene, in which 1 or 2 C are replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene, in which 1 or 2 C are optionally replaced by C, up to 12 single H of CH 2-group of the alkyl is optionally replaced by F, Cl, Br, I, CN or linear up to 18C-alkyl, in which 1-6 CH 2-units are optionally replaced by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which one CH unit is optionally replaced by N, CC, 1,2-, 1,3- or 1,4-substituted phenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene, in which 1 or 2 C are optionally replaced by N, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2.10- or 9.10- disubstituted anthracene in which 1 or 2 C are optionally replaced by N, where instead of being able to carry substituents, the free valences of the methine or quaternary carbon atoms are associated in pairs to form rings, such as cyclohexane; and Y1 : CHO, aldimino whose part is again replaced by R1, also a second connected chromophore, in which Y1 is connected with two units of X, a corrole unit e.g. 5,15- (2,6-dichlorophenyl)corrole unit connected in position 10 or a perylene-3,4:9,10-tetracarboxylic acid bisimide unit connected with N, whose another N atom is bonded with a solubility enhancing group e.g. 1-hexylheptyl, 2,5-di-tert-butylphenyl or 2,6-di-iso-propyl, where the perylene core is optionally substituted with donor group e.g. ether, preferably with phenoxy group at 1, 6, 7 or 12th position. An independent claim is included for optical excitation of (Q) using available light sources such as daylight, indium lamp light (both preferred), mercury vapor lamp or xenon high-pressure mercury lamp. [Image].