Nonlinear Optical Chromophores Containing 3-Aminocyclohex-2-en-1-one Based Donor Groups, and Methods of Making and Using the Same

An electro-optic device comprising one or more resistive film, wherein the one or more resistive film each comprising a nonlinear optical chromophore dispersed and poled within a host polymer matrix, wherein the nonlinear optical chromophore of a general formula (I):

• D
• -
• Π
• -
• A
• (
• I
• )
• wherein D represents an organic electron-donating group;
• A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D;
• and Π represents a Π-bridge between the organic electron-accepting group and the organic electron-donating group;
• wherein D comprises 3-aminocyclohex-2-en-1-one based donors having a formula (D1):
• wherein R1 and R4 each independently represents a moiety selected from the group consisting of H, heteroatoms, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted thioalkyl, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C2-C10 linear or branched alkenyl, substituted or unsubstituted C2-C10 linear or branched alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and CH3—(CH2)n—O—(CH2)n where n is 1-10;
• and
• wherein R5, R6, R7, R8, R9, R10, and R11 each independently represents a moiety selected from the group consisting of hydrogen, heteroatoms, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted thioalkyl, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C2-C10 linear or branched alkenyl, substituted or unsubstituted C2-C10 linear or branched alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH2)n—O—(CH2)n where n is 1-10.