A novel amphiphilic ferrocene derivative containing a barbituric acid unit: synthesis and quadratic optical non-linearity

• Published in: Thin solid films Vol. 284; pp. 859 - 862
• Main Authors: Cao, Y.-W., Chai, X.-D., Yang, W.-S., Lu, R., Jiang, Y.-S., Li, T.-J., Blanchard-Desce, M., Lehn, J.-M.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.09.1996
• Subjects: Ferrocene; Langmuir-Blodgett films; Monolayers; Second harmonic generation; π-donor-switch-acceptor; Second harmonic generation; Langmuir-Blodgett films; Monolayers; Ferrocene; π-donor-switch-acceptor
• ISSN: 0040-6090; 1879-2731
• DOI: 10.1016/S0040-6090(95)08463-0

A novel amphiphilic ferrocene derivative ( P) containing barbituric acid was designed and synthesized. It has a π-donor-switch-acceptor structure, in which the N, N-dioctadecylaniline unit serves as the electron donor, the ferrocene moiety as the switch, and the barbituric acid unit as the electron acceptor. The non-linear optical experiments show the lipid P displays efficient optical second harmonic generation (SHG) with a molecular hyperpolarizability (β) as high as 1.8 × 10 −28 e.s.u. The lipid P alone is unable to form a high quality monolayer at the gas-water interface. The molecular recognition of the lipid P and its complementary substrate-melamine derivative ( M), at the gas-water interface, may significantly improve the monolayer formation of the lipid P. The improvement of the monolayer has been found to exhibit a temperature-dependent effect: at about 24.5 °C it reaches the optimum.