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AssigneeHoechst Aktiengesellschaft
InventorsRudolf Gompper, Harald Engel, Donald Lupo
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Aromatic, substituted pyrimidine compounds, methods for the preparation thereof, and use thereof Compounds having a pyrimidine ring, of the formula (I) ##STR1## are suitable for nonlinear-optical applications, e.g. for fabricating components for frequency-doubling of light. In the formula, AX is ##STR2## An.sup.- is an anion, B is the pyrimidine(1,4) radical, D is --NH.sub.2, --NH--NH.sub.2, --OR.sup.6, --O(CH.sub.2).sub.p OH, --OH, --NR.sup.5 R.sup.6, --NHR.sup.6, --N.dbd.CH--R.sup.4, --HN--N.dbd.CH--R.sup.4, --NO.sub.2, the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.5 are an alkyl radical having from 1 to 22 carbon atoms or a radical CF.sub.3 (CF.sub.2).sub.m (CH.sub.2).sub.n, R.sup.4 is a phenyl radical which may be substituted, R.sup.6 is an alkyl radical having from 1 to 22 carbon atoms or the radical CF.sub.3 (CF.sub.2).sub.m (CH.sub.2).sub.n, where m is an integer of at least 5, n is an integer of at least zero, and (n+m) is at most 22, or the group (CH.sub.2).sub.p OH, where p is an integer from 2 to 5.
A non-linear optical material comprising a compound having a pyrimidine ring, of the formula (I) ##STR33## in which AX is selected from the group consisting of ##STR34## An.sup.- is an anion, B is ##STR35## D is selected from the group consisting of --NH.sub.2
A compound of the formula ##STR36## wherein D is NO.sub.2 and, AX is ##STR37## R.sup.3 is an alkyl radical having from 1 to 22 carbon atoms or a radical CF.sub.3 (CF.sub.2).sub.m (CH.sub.2).sub.n, where m is an integer of at least 5 and n is an integer of at least zero and (n+m) is at most 22, and An.sup.(-) is an anion, and B is ##STR38##
A compound having the formula II ##STR39## wherein AX is ##STR40## An.sup.(-) is an anion, D is OR.sup.2, OH, NH.sub.2, NH--NH.sub.2,
A compound having the formula III ##STR41## wherein AX is ##STR42## R.sup.3 is an alkyl radical having from 1 to 22 carbon atoms or a radical CF.sub.3 (CF.sub.2).sub.m (CH.sub.2).sub.n, where m is an integer of at least 5 and n is an integer of at least zero and (n+m) is at most 22,
A compound of the formula IV ##STR43## wherein X is ##STR44## and An.sup.(-) is an anion.
A compound of formula I ##STR45## in which AX is ##STR46## An.sup.- is an anion, B is ##STR47## D is selected from the group consisting of --NH.sub.2
A compound of formula I ##STR48## wherein AX is selected from the group consisting of ##STR49## An.sup.- is an anion, B is ##STR50## D is OR.sup.2, --N.dbd.CHR.sup.4, NR.sup.5 R.sup.6, or --NH--N.dbd.CHR.sup.4
A layer element containing at least one monomolecular regularly arranged layer of an amphiphilic compound on a substrate, wherein the amphiphilic compound is a compound having a pyrimidine ring, of the formula (I) ##STR51## in which AX is selected from the group consisting of ##STR52## An.sup.- is an anion, B is ##STR53## D is selected from the group consisting of --NH.sub.2
A component for frequency-doubling of light, in which there is arranged on a substrate a layer of an NLO-active material, whose refractive index is higher than that of the substrate, and the component contains means for irradiation with light and reradiation of light, wherein the NLO-active material employed is a compound having a pyrimidine ring, of the formula (I) ##STR54## in which AX is selected from the group consisting of ##STR55## An.sup.- is an anion, B is ##STR56## D is selected from the group consisting of --NH.sub.2
A non-linear optic device comprising a compound of the formula I ##STR57## in which AX is selected from the group consisting of ##STR58## An.sup.(-) is an anion B is ##STR59## D is selected from the group consisting of --NH.sub.2
A process for preparing compounds of the formula V ##STR60## wherein ##STR61## and D.dbd.OCH.sub.3, NO.sub.2 or OH,
A process for preparing compounds of the formula VIII ##STR64## wherein D=OCH.sub.3, NO.sub.2, or OH, which comprises reacting a vinamidinium salt of the formula IX ##STR65## and An.sup.(-) is an anion, wherein D is OCH.sub.3, NO.sub.2 or OH, with 4-pyridinecarbamidine hydrochloride (formula X) ##STR66## in methanolic sodium methylate solution.
A process for preparing compounds of the formula (XI) ##STR67## wherein D=OCH.sub.3 or NO.sub.2, which comprises reacting a vinamidinium salt of the formula XII wherein An.sup.(-) is an anion ##STR68## with a benzamidine hydrochloride of the formula XIII ##STR69## wherein D is NO.sub.2 or OCH.sub.3, in methanolic sodium methylate solution.
A component in a liquid-crystal mixture, said component comprising a compound of the formula XIV ##STR70## wherein R.sup.a is ##STR71## or OR and R is a C.sub.4 -C.sub.22 -alkyl radical.
A component in a liquid-crystal mixture, said component comprising a compound of the formula XV ##STR72## wherein AX is ##STR73## and R is methyl or AX is ##STR74## and R is R.sup.1, An.sup.(-) is an anion, and,
A liquid-crystal mixture containing a compound of the formula XIV ##STR75## wherein R.sup.a is ##STR76## or OR and R is a C.sub.16 -C.sub.22 -alkyl radical.
A liquid-crystal mixture containing a compound of the formula XV ##STR77## wherein AX is ##STR78## and R is methyl or AX is ##STR79## and R is R.sup.1, An.sup.(-) is an anion, and,
A compound having a pyrimidine ring, of the formula (I) ##STR80## in which AX is selected from the group consisting of ##STR81## An.sup.- is an anion, B is ##STR82## D is selected from the group consisting of --NH.sub.2
A compound having a pyrimidine ring, of the formula (I) ##STR83## in which AX is selected from the group consisting of ##STR84## An.sup.- is an anion, B is ##STR85## D is selected from the group consisting of --NH.sub.2
A process for preparing compounds of the formula V ##STR86## wherein ##STR87## and D=OCH.sub.3 or OH, which comprises reacting a vinamidinium salt of the formula VI ##STR88## wherein D is OCH.sub.3 or OH, and An.sup.(-) is an anion, with a benzamidine hydrochloride of the formula VII ##STR89## wherein A is NO.sub.2 or OCH.sub.3, in anhydrous pyridine.
A process for preparing compounds of the formula V ##STR90## wherein ##STR91## and D=OCH.sub.3, NO.sub.2 or OH, which comprises reacting a vinamidinium salt of the formula VI ##STR92## wherein D is OCH.sub.3, NO.sub.2 or OH, and An.sup.(-) is an anion, with a benzamidine hydrochloride of the formula VII ##STR93## wherein A is OCH.sub.3, in anhydrous pyridine.
Dependencies are inferred from the claim text.