Sterically stabilized polyene-bridged second-order nonlinear optical chromophores and devices incorporating the same

A nonlinear optical device comprising:

• an active element including a chromophore formed as
• wherein D is an electron donor group;
• wherein A is an electron acceptor group;
• wherein a conjugate diene in the bridge structure connects the bridge ring structure and the acceptor A;
• wherein R=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same;
• wherein R′=methyl group;
• wherein the acceptor is formed as
• wherein R=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same;
• wherein R″=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group, with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R′ is not methyl when the two R′ groups are the same.

A nonlinear optical device comprising:

• an active element including a chromophore formed as:
• wherein D is an electron donor group;
• wherein A is an electron acceptor group;
• wherein a conjugate diene in the bridge structure connects the bridge ring structure and the acceptor A;
• wherein R=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same.

A nonlinear optical device comprising:

• an active element including a chromophore formed as
• wherein D is an electron donor group;
• wherein A is an electron acceptor group;
• wherein R=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same.

A nonlinear optical device comprising:

• an active element formed from a chromophore including
• an electron donor group,
• an electron acceptor group, and
• a π-conjugate bridge structure between the electron donor group and the electron acceptor group;
• wherein the bridge structure includes at least one non-aromatic ring which lock(s) one or two carbon-carbon double bond(s) of of the conjugate bridge structure;
• wherein the ring(s) is(are) five-, six- or seven-membered;
• wherein the electron acceptor group is connected to the bridge ring structure with a conjugated diene or triene.

A nonlinear optical device comprising:

• an active element formed from a chromophore including
• an electron donor group,
• an electron acceptor group, and
• a π-conjugate bridge structure between the electron donor group and the electron acceptor group;
• wherein the bridge contains a bithiophene unit formed as
• wherein R=any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same;
• wherein at least one of the R groups on the bithiophene has more than one carbon.

A nonlinear optical device comprising:

• an active element formed from a chromophore including
• an electron donor group,
• an electron acceptor group, and
• a bithiophene-containing bridge structure between the electron donor group and the electron acceptor group;
• wherein the acceptor is formed as
• wherein R=any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same.

A nonlinear optical device comprising:

• an active element formed from a chromophore including
• an electron donor group,
• an electron acceptor group, and
• a bithiophene-containing bridge structure between the electron donor group and the electron acceptor group;
• wherein the acceptor is formed as
• wherein R=any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same.

A nonlinear optical device comprising:

• an active element formed from a chromophore including
• an electron donor group,
• a ring-locked tricyano electron acceptor, and
• a π-conjugated bridge structure between the electron donor group and the electron acceptor;
• wherein the ring-locked tricyano electron acceptor comprises
• wherein R=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R groups at different positions are not necessarily the same;
• wherein R′=H, F, or any perhalogenated, halogenated or non-halogenated aliphatic or aromatic group, with 1-30 carbon atoms functionalized with zero or more of the following functional groups:
• hydroxy, ether, ester, amino, silyl, and siloxy, and R′ is not methyl or n-butyl when the two R′ groups are the same.