Nonlinear Optical Chromophores with Indolizine Donor Groups

Patent metadata

Field	Value
Publication number	US-2025011321-A1
Application number	US-202418756051-A
Country	US
Kind code	A1
Filing date	Jun 27, 2024
Priority date	Jun 29, 2023
Publication date	Jan 9, 2025
Grant date	—

Abstract

The present invention is directed, in general, to nonlinear optical chromophores having an indolizine donor group. Various embodiments of the present invention include nonlinear optical chromophores with indolizine donor group having an indolizine donor connected to a II-bridge group. In various preferred embodiments of the present invention, the indolizine donor groups may be substituted or unsubstituted, including hydro and alkyl substituents, aryl substituents and combination thereof. In certain embodiments of the present invention, the substituent moieties in the indolizine donor groups may be important for isolation. The isolation may reduce chromophore-chromophore interaction. The isolation may reduce charge transfer between molecules. The isolation may increase maximum applied voltage, which may contribute to more optimal poling and higher r 33 .

First claim

What is claimed is:

1 . A nonlinear optical chromophore of the general formula (I):
D - II - A   (I)
wherein D represents an organic indolizine electron-donating group having the following formula (D a ):

wherein R 1 in the indolizine electron-donating group represents a moiety selected from the group consisting of H, substituted or unsubstituted C 2 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, and substituted or unsubstituted C 2 -C 10 alkynyl, wherein R 2 in the indolizine electron-donating group represents a moiety selected from the group consisting of substituted monocyclic aryl, substituted or unsubstituted polycyclic aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, and substituted or unsubstituted cyclohexyl;
wherein A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and II represents a II-bridge between A and D, wherein the II-bridge comprises a carbon chain covalently bound to and separating A and D.

2 . The nonlinear optical chromophore according to claim 1 , wherein the carbon chain length between A and D is 6 to 8 carbon atoms.

3 . The nonlinear optical chromophore according to claim 1 , wherein the carbon chain length between A and D is 4 carbon atoms.

4 . The nonlinear optical chromophore according to claim 1 , wherein the carbon chain length between A and D is 10 carbon atoms.

5 . The nonlinear optical chromophore according to claim 2 , wherein the Amax value is in a range of 670 nm and 875 nm.

6 . The nonlinear optical chromophore according to claim 2 , wherein the Δλ max value is equal to or smaller than 130 nm.

7 . The nonlinear optical chromophore according to claim 2 , wherein II represents a II-bridge between A and D having the following formula (II a ):

wherein R 3 represents a moiety selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, and substituted or unsubstituted cyclohexyl; wherein R 6 represents a moiety selected from the group consisting of H, halogen molecule, substituted or unsubstituted C 2 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, and substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, and substituted or unsubstituted cyclohexyl; and wherein a is an integer of 1 or 2.

8 . The nonlinear optical chromophore according to claim 1 , wherein A represents an electron-accepting group of the general formula (A a ):

wherein R 4 and R 5 each independently represents a moiety selected from the group consisting of H, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH 2 ) n —O—(CH 2 ) n where n is 1-10.

9 . The nonlinear optical chromophore according to claim 1 , wherein the nonlinear chromophore has the general formula (C′):

10 . A nonlinear optical chromophore of the general formula (I):
D - II - A   (I)
wherein D represents an organic indolizine electron-donating group having the following formula:

wherein R 1 , R 2 , R 3 and R 4 each independently represents a moiety selected from the group consisting of heteroatoms, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, or (CH 2 ) n —O—(CH 2 ), where n is 1-10, and wherein R 5 represents a moiety selected from the group consisting of H or substituted or unsubstituted aryl;
wherein A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and/7 represents a II-bridge between A and D, wherein the/7-bridge comprises a carbon chain covalently bound to and separating A and D.

11 . The nonlinear optical chromophore according to claim 10 , wherein R 5 represents a phenyl moiety.

12 . The nonlinear optical chromophore according to claim 10 , wherein II represents a II-bridge between A and D having the following formula (II a ):

wherein R 3 represents a moiety selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, and substituted or unsubstituted cyclohexyl; wherein R 6 represents a moiety selected from the group consisting of H, halogen molecule, substituted or unsubstituted C 2 -C 10 alkyl, substituted or unsubstituted C 2 -C 10 alkenyl, and substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, and substituted or unsubstituted cyclohexyl; and wherein a is an integer of 1 or 2.

13 . The nonlinear optical chromophore according to claim 10 , wherein A represents an electron-accepting group of the general formula (A a ):

wherein R 4 and R 5 each independently represents a moiety selected from the group consisting of H, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, and (CH 2 ) n —O—(CH 2 ) n where n is 1-10.

14 . A nonlinear optical chromophore of the general formula (I):
D - II - A   (I)
wherein D represents an organic indolizine electron-donating group having one of the following formulas:

wherein R 5 represents a moiety selected from the group consisting of H or substituted or unsubstituted aryl;
wherein A represents an organic electron-accepting group having an electron affinity greater than the electron affinity of D; and II represents a II-bridge between A and D, wherein the II-bridge comprises a carbon chain covalently bound to and separating A and D.

15 . The nonlinear optical chromophore according to claim 14 , wherein R 5 re

Assignees

• Lightwave Logic Inc

Inventors

• Ramann Ginelle A
• Johnson Barry L
• Pecinovsky Cory

Classifications

• G02F1/3613

  containing Sulfur · CPC title

• G02F1/3612

  Heterocycles having N as heteroatom · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C09B23/0066 Primary

  the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid) · CPC title