Water-soluble distyrylbenzene chromophores for applications in optoelectronic technologies
AssigneeThe Regents of the University of California
InventorsGuillermo C. Bazan, Bernhard Koehler, Alexander Mikhailovsky, Hadjar Benmansour, Bin Liu, Janice W. Hong
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Abstract
Two-photon or multi-photon chromophores having a conjugated pi-electron system with donating groups at each end of the pi-electron system providing charge-transfer properties, and having quaternary amine groups that can enhance the solubility of the chromophore in water. In a particular embodiment, the chromophore is based on a distyrylbenzene core, with donor or acceptor groups attached to the central benzene ring.
Claims16
A chromophore having the following structural formula (I):
- wherein Ar1, Ar2 and Ar3 are each independently a substituted or non-substituted aromatic hydrocarbon or aromatic heterocyclic ring;
- Ak1, Ak2, Ak3 and Ak4 are each independently a substituted or non-substituted alkyl or alkylene group;
- R1, R2 and R3 are each independently a substituted or non-substituted alkyl group;
- and X1 is a counter anion.
A distyrylbenzene chromophore having the following structural formula (II):
- wherein A1 and A2 are each independently a hydrogen, or a donor or acceptor group;
- and R is [(CH2)n]6—NR′3X, where R′ is (CH2)m—H, X is any anion, n is from 1 to 10 and m is from 1 to 10.
A distyrylbenzene chromophore having the following structural formula (III):
- wherein R is (CH2)6—NR′3X, R′ is CH3, and X is any anion.
A distyrylbenzene chromophore having the following structural formula (IV):
- wherein R is (CH2)6—NR′3X, R′ is CH3 and X is any anion.
A method of preparing a distyrylbenzene chromophore, comprising reacting a 1,4-dibenzylphosphonate with a haloalkylamino-benzaldehyde and adding a trialkylamine by condensation to said distyrylbenzene chromophore whereby to provide water solubility to said chromophore.
A method of preparing a water-soluble two-photon absorbing distyrylbenzene chromophore, comprising the following steps:
- a) reacting analine 6-chloro-1-hexanol and potassium carbonate to yield N,N-Bis-(6-hydroxyhexyl)-aniline of the formula:
- b) reacting N,N-Bis-(6-hydroxyhexyl)-aniline and phosphorous oxychloride to yield N,N-Bis-(6-chlorohexyl)-4-amino)-benzaldehyde of the formula:
- c) reacting N,N-Bis-(6-chlorohexyl)-4-amino)-benzaldehyde and sodium iodide to yield N,N-Bis-(6-iodohexyl)-4-amino-benzaldehyde of the formula:
- d) reacting N,N-Bis-(6-iodohexyl)-4-amino-benzaldehyde and 1,4-dibenzylphosphonate of the formula
- to yield a precursor chromophore of the formula:
- e) reacting the precursor chromophore with trimethylamine to yield a distyrylbenzene chromophore of the formula:
Dependencies are inferred from the claim text.