Spiroconjugated charge-transfer dyes for optical applications

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

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544231, 544 6, 5483011, 548147, 549336, 549 17, 549 16, 549 32, C07D27764, C07D23512, C07D24304, C07D23970

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055918484

ABSTRACT:
New intramolecular charge-transfer organic dyes are described. The design of these molecules is based on the phenomenon of spiroconjugation, and it provides a modular approach to the preparation of unique materials with interesting optical properties. In the dyes of the invention, the lowest unoccupied molecular orbital (LUMO) of the acceptor part (based on indandione) is spiroconjugated with the highest unoccupied molecular orbital (HOMO) of the donor part (amines, alcohols and thiols). The interaction between the donor and acceptor is controlled by the energy and symmetry of the frontier orbitals. The novel dyes described herein, with predictable and tunable optical properties, can be used in many optical applications including nonlinear optics (NLO).

REFERENCES:
Gleiter, R. et al. Chem. Ber. 127, 2215-2224 (1994).

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