Chiral pyrrolo[1,2-a]quinolines as second-order nonlinear optical materials


Kelderman, E. and Verboom, W. and Engbersen, J.F.J. and Harkema, S. and Heesink, G.J.T. and Lehmusvaara, E. and Hulst, N.F. van and Reinhoudt, D.N. and Derhaeg, L. and Persoons, A. (1992) Chiral pyrrolo[1,2-a]quinolines as second-order nonlinear optical materials. Chemistry of Materials, 4 (3). pp. 626-631. ISSN 0897-4756

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Abstract:The synthesis and nonlinear optical properties of a series of chiral pyrrolo[1,2-a]quinolines la-e is presented. The microscopic hyperpolarizabilities (beta(z)) were determined by EFISH measurements and the macroscopic susceptibilities (X2) were estimated by the Kurtz powder test. A small fixed angle of the annelated pyrrolidine donor unit with respect to the aromatic-pi-system renders the whole donor-pi-acceptor system chiral. The small deviation from planarity of approximately 10 +/- 3-degrees causes no observable reduction of the microscopic beta(z) value in comparison with the planar conjugated N,N- dimethylaniline analogues. The powder test showed phase matching for all pyrrolo[1,2-a]quinolines with an electron- withdrawing substituent at C-7 (1b-e). The aldehyde 1b crystallizes in the P2(1)2(1)2(1) space group and was calculated to have an efficiency of 8.3% of beta under optimal phasematch conditions. The nitro derivative 1c crystallizes in the favorable space group P2(1) (Z = 2) in which the angles of the two independent molecules with the optical b axis are 71.7- degrees and 43.5-degrees.
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Copyright:© 1992 American Chemical Society
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