Thiazolemethine dyes

Details Thiazolemethine dyes Thiazolemethine dyes

1996-10-24

1998-02-03

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548193, 546165, 546171, C07D277587, C07D41712

Patent

active

057146160

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP95/01348 filed Apr. 12, 1995.
The present invention relates to novel methine dyes of the formula I ##STR3## where R is hydrogen, unsubstituted or substituted C.sub.1 -C.sub.10 -alkyl or unsubstituted or substituted phenyl, CH.dbd.CH--CH.dbd.CH--CH, ##STR4## where Q.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, chlorine or bromine and Q.sup.2 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and aminothiazole or aminothiophene series, the aniline series, to the use thereof in nonlinear optics and to novel thiazole derivatives.
U.S. Pat. No. 5,364,919 discloses the use of methine dyes in polymeric nonlinear optical systems.
It is an object of the present invention to provide novel methine dyes which are advantageously suitable for use in polymeric nonlinear optical systems. In particular, dyes of this type ought to have large hyperpolarizability values, good thermal stability, good compatibility with the polymers used in nonlinear optical systems and good film-forming properties with copolymers.
We have found that this object is achieved by the methine dyes of the formula I defined at the outset.
Examples of suitable radicals Y are those of the formulae IIa to IIi ##STR5## where n is 0 or 1, or 2 oxygen atoms in ether functionalities, C.sub.1 -C.sub.4 -alkoxy, especially methoxy or ethoxy, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.1 -C.sub.4 -mono- or dialkylaminosulfonylamino or --NHCOZ.sup.7 or --NHCO.sub.2 Z.sup.7 where Z.sup.7 is phenyl, benzyl, tolyl or C.sub.1 -C.sub.10 -alkyl which may be interrupted by 1 or 2 oxygen atoms in ether functionalities, -C.sub.4 -alkoxy, especially methoxy or ethoxy, of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl which may be substituted and may be interrupted by 1 or 2 oxygen atoms in ether functionalities, C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or tolyl or together with the nitrogen atom connecting them a 5- or 6-membered saturated heterocyclic radical which may contain further heteroatoms, substituted phenyl, unsubstituted or substituted benzyl, cyclohexyl, thienyl, hydroxyl or C.sub.1 -C.sub.10 -monoalkylamino.
All the alkyl and alkenyl groups occurring in the abovementioned formulae may be either straight-chain or branched.
Examples of suitable substituents for substituted alkyl groups in the abovementioned formulae are, unless stated otherwise, cyano, phenyl, tolyl, hydroxyl, C.sub.1 -C.sub.6 -alkanoyloxy, acryloyloxy, methacryloyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylaminocarbonyloxy or C.sub.1 -C.sub.4 -alkoxycarbonyloxy, it being possible in the latter case for the alkoxy group to be substituted by phenyl or C.sub.1 -C.sub.4 -alkoxy. As a rule, the alkyl groups then have 1 or 2 substituents.
Examples of suitable substituents for substituted phenyl groups in the abovementioned formulae are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.6 -alkanoyloxy, acryloyloxy or methacryloyloxy. As a rule, the phenyl groups then have 1 to 3 substituents.
Examples of suitable Q.sup.1, Q.sup.2, R, Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4, Z.sup.6 and Z.sup.7 radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
Further examples of R, Z.sup.1, Z.sup.3, Z.sup.4, Z.sup.6 and Z.sup.7 are pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl (the names isooctyl, isononyl and isodecyl are trivial names derived from the alcohols obtained by oxo synthesis, cf. Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A1, pages 290 to 293, and Vol. A 10, pages 284 and 285).
Further examples of Z.sup.1, Z.sup.3, Z.sup.4 and Z.sup.7 are 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dio

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J. Org. Chem., vol. 54, No. 16, 1989, 3775 to 3778, Determining Second-Order Polarizabilities, Paley, et al.
Chemistry & Industry, Oct. 1, 1990, Polymers for Non-Linear Optical Devices, Carole Jones, 600-608.
Wurthner et al., Chemical Physics 173 (1993) 305-314, North-Holland, Second-Order Polarizability of Donor-Acceptor Substituted Oligothiophenes: Substituent Variation and Conjugation Length Dependence.
Wortmann, et al., Chemical Physics 173 (1993) 99-108, North-Holland, Deviations from Kleinman Symmetry of the Second-Order Polarizability Tensor in Molecules with Low-Lying Perpendicular Electronic Bands.
J. Phys. Chem. (1992), 96, 9724-9730, Wortmann, et al., Electrooptical Absorption Measurements of Phototautomerizing Systems S.sub.0 and S.sub.1 Static Polarizabilities of Bipyridinediols.

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