Synthesis of an isophorone-based nonlinear optical chromophore

Synthetic Communications

Volumn 34, Issue 18, 2004, Pages 3419-3429

  Davis, Matthew C ^a   Chafin, Andrew P ^a   Hollins, Richard A ^a   Baldwin, Lawrence C ^a   Erickson, Eric D ^a   Zarras, Peter ^a   Drury, Elliott C ^a,b  

^a NAVAL AIR WARFARE CENTER   (United States)

^b NAWCWD   (United States)

Author keywords

Aldol; Dyes; Knoevenagel; Nonlinear optical; Vilsmeier

Indexed keywords

ISOPHORONE;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; KNOEVENAGEL CONDENSATION; NONLINEAR SYSTEM; OPTICAL DENSITY; RIGIDITY; SYNTHESIS;

EID: 5444254662     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200030646     Document Type: Article

References (15)

1. Prasad, P.N.; Williams, D.J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; John Wiley & Sons: New York, 1991.
2. Ahlheim, M.; Barzoukas, M.; Bedworth, P.V.; Blanchard-Desce, M.; Fort, A.; Hu, Z.-Y.; Marder, S.R.; Perry, J.W.; Runser, C.; Stähelin, M.; Zysset, B. Chromophores with strong heterocyclic acceptors: a poled polymer with a large electro-optic coefficient. Science 1996, 271 (5247), 335-337.
3. π electrooptic modulators from CLD-1: chromophore design and synthesis, material processing, and characterization. Chem. Mater. 2001, 13 (9), 3043-3050.
4. Marson, C.M.; Giles, P.R. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, USA, 1994.
5. Kabas, G. The condensation of aromatic aldehydes with isophorone. Tetrahedron 1966, 22, 1213-1218.
6. Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F. Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols. Tetrahedron 1994, 50 (39), 11499-11508.
7. Nivalkar, K.R.; Mudaliar, C.D.; Mashraqui, S.H. Micelles in organic synthesis: Aldol reactions in aqueous micelles of cetyltrimethylammonium bromide. J. Chem. Res. (S) 1992, 3, 98-99.
8. Wittig, G.; Reiff, H. Directed aldol condensations. Angew. Chem. Int. Ed. Engl. 1968, 7 (1), 7-14.
9. Wittig, G.; Suchanek, P. Über gezielte aldolkondensationen-II. Tetrahedron 1966, 22 (Suppl. 8, Part I), 347-358.
10. Wittig, G.; Hesse, A. Directed aldol condensations: β- phenylcinnamaldehyde. Org. Synth. Coll Vol. VI, 901-905.
11. Melikian, G.; Rouessac, F.P.; Alexandre, C. Synthesis of substituted dicyanomethylendihydrofurans. Synth. Commun. 1995, 25 (19), 3045-3051.
12. He, M.; Leslie, T.M.; Sinicropi, J.A. α-hydroxy ketone precursors leading to a novel class of electro-optic acceptors. Chem. Mater. 2002, 14 (5), 2393-2400.
13. Goldsmith, D. Piperidine. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; John Wiley & Sons, Inc.: Chichester, England, 1995; Vol. 6, 4152-4154.
14. House, H.O. The aldol condensation and related reaction reactions. In Modern Synthetic Reactions, 2nd Ed.; W.A. Benjamin, Inc.: Menlo Park, CA, 1972; 646-653.
15. He, M.; Leslie, T.M.; Sinicropi, J.A.; Garner, S.M.; Reed, L.D. Synthesis of chromophores with extremely high electro-optic activities. 2. Isophorone- and combined isophorone-thiophene-based chromophores. Chem. Mater. 2002, 14 (11), 4669-4675.