Patent DE-102008058454-A1 (DE)
Title: Use of an alpha effective compound, and an isoxazolidine compound e.g. as an electron donor group in light-driven systems for charge separation, to extract solar energy, preferably in photovoltaic cells, and for mass coloring of polymers
Inventor: LANGHALS HEINZ
IPC: C09D11/00
Filed: 2008-11-21
Abstract: Use of alpha -effective compound (I), and an isoxazolidine compound (II), as an electron donor group in light-driven systems for charge separation, is claimed. Use of alpha -effective compound of formula (X(R 1>)(R 3>)-Y 1>(R 2>)(R 3>)) (I), and isoxazolidine compound of formula (II), as an electron donor group in light-driven systems for charge separation, is claimed. X, Y 1>elements with free, non-binding electron pairs, preferably element from II or III group, N, O, F, S or Cl, preferably elements from II group, N or O; and R 1>-R 5>H, linear 1-37C-alkyl, in which 1-10 CH 2units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH = CH-, and one CH unit is optionally substituted by N, acetylenic C?=C-groups, 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 napthalene, in which 1-2 CH-groups are optionally substituted 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 substituted by N, where 2-12 single H atoms of the CH 2-groups are optionally substituted by halo, or CN or a linear 2-18C-alkyl, in which 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which one CH unit is optionally substituted by N, acetylenic C?=C-groups, 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 napthalene in which one or two carbon atoms are optionally substituted 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 carbon atoms are optionally substituted by N, where 2-12 single H atoms of the CH 2-group of the alkyl residue is optionally substituted by F, Cl, Br, or CN, or linear 2-18C-alkyl, in which 1-6 CH 2units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-, in which a CH unit is optionally substituted by N, acetylenic C=C-groups 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 napthalene, in which one or two carbon atoms are optionally substituted by N, or 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 carbon atoms are optionally substituted by N. Where instead of substituents, the free valency of the methine group and/or quaternary C-atom are pair-wise connected to form rings, e.g. cyclohexane ring, and the residues of R 1>-R 9>are optionally substituted by F, Cl, Br or I. Independent claims are included for: (1) a perylene bisimide-dyaden compound of formula (III); (2) a perylenetetracarboxylic acid bisimide-nitrone compound of formula (IV); (3) the preparation of (III); and (4) the preparation of (IV) comprising reacting perylenebisimide-aldehyde and hydroxylamine derivative, which is N-methyl hydroxylamine or N-phenyl hydroxylamine. R 6>-R 10>R 1>; and X : 1-12 CH 2units, which is optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which one CH unit is optionally substituted by N, acetylenic C?=C-groups, 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 napthalene, in which 1-2 CH groups are optionally substituted 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 1-2 CH groups are optionally substituted by N, where 2-12 single H atoms of CH 2-group are optionally substituted by F, Cl, Br, I or CN, or a linear 2-18C-alkyl, in which 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which one CH unit is optionally substituted by N, acetylenic C=C-groups, 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 napthalene, in which 1-2C atoms are optionally substituted 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 1-2C atoms are optionally substituted by N, where 2-12 single H of CH 2-group of alkyl residue is optionally substituted by halo, CN or linear 2-18C-alkyl, in which 1-6 CH 2-units are optionally substituted by carbonyl, O, S, Se, Te, cis or trans-CH=CH-groups, in which a CH unit is optionally substituted by N, acetylenic C?=C-groups, 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 napthalene, in which 1-2C are optionally substituted by N, or 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 1-2C are optionally substituted by N. Where instead of substituents, the free valency of the methine group and/or quaternary C-atom are pair-wise connected to form rings, e.g. cyclohexane ring, and the residues of R 6>-R 8>are optionally substituted by F, Cl, Br or I. [Image] [Image] [Image].