University of Minnesota

Gayle M Frankenbach

Margaret C Etter

Thomas W Panunto

Optically nonlinear aromatic carboxylic acid cocrystals are provided of the formula: ##STR1## wherein each R is CN or NO.sub.2, n is 1-4, m is 1-3 and X and Y are individually (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)-alkanolyl, (C.sub.1 -C.sub.3)alkoxycarbonyl, ar(C.sub.1 -C.sub.5)alkyl, aryl, (C.sub.1 -C.sub.3)alkoxy, hydroxy, halo or mixtures thereof.

Optically nonlinear aromatic carboxylic acid complexes

Optically nonlinear aromatic carboxylic acid cocrystals are provided of the formula: ##STR1## wherein each R is CN or NO.sub.2, n is 1-4, m is 1-3 and X and Y are individually (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)alkanolyl, (C.sub.1 -C.sub.3)alkoxycarbonyl, ar(C.sub.1 -C.sub.5)alkyl, aryl, (C.sub.1 -C.sub.3)alkoxy, hydroxy, halo or mixtures thereof.

Compounds capable of second harmonic generation are provided for use in a nonlinear optical device, in combination, a harmonic-generating medium, means for introducing coherent radiation into said harmonic-generating medium, and means for utilizing the coherent radiation emitted from said medium, wherein said medium consists essentially of a crystalline body of a compound of the formula: ##STR1## wherein n is about 0-5, m is about 0-5, R.sup.1 is individually --NO.sub.2, --OR.sup.2, --CH, --NR.sup.2 R.sup.3, (C.sub.1 -C.sub.5)alkyl, --CO.sub.2 H, halo, ##STR2## R is individually --NO.sub.2, --CH.sub.3, --OR.sup.2, --NR.sup.2 R.sup.3, --CN, ##STR3## and X is --O--, --S--, --N(R.sup.2)--, ##STR4## or --C.tbd.C--; and wherein R.sup.2 and R.sup.3 are individually H, (C.sub.1 -C.sub.5 alkyl, aryl or ar(C.sub.1 -C.sub.5)alkyl.

Optically nonlinear pyridine-N-oxide complexes

Compounds capable of second harmonic generation are provided for use in a nonlinear optical device, in combination, a harmonic-generating medium, means for introducing coherent radiation into said harmonic-generating medium, and means for utilizing the coherent radiation emitted from said medium, wherein said medium consists essentially of a crystalline body of a compound of the formula: ##STR1## wherein n is about 0-5, m is about 0-5, R.sup.1 is individually --NO.sub.2, --OR.sup.2, --CN, --NR.sup.2 R.sup.3, (C.sub.1 -C.sub.5)alkyl, --CO.sub.2 H, halo, ##STR2## R is individually --NO.sub.2, --CH.sub.3, --OR.sup.2, --NR.sup.2 R.sup.3, --CN, ##STR3## and X is --O--, --S--, --N(R.sup.2)--, ##STR4## and wherein R.sup.2 and R.sup.3 are individually H, (C.sub.1 -C.sub.5)alkyl, aryl or ar(C.sub.1 -C.sub.5)alkyl.

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Minneapolis, MN, United States of America

Gayle M Frankenbach