Synthesis and monolayer spreading behaviour of surface-active compounds containing electron- and hole-transporting groups. 1. Fluorenylidene derivatives

Abstract

. Surface-active derivatives containing fluorenylidene groups were synthesized, with the goal of creating thin-film devices incorporating monolayers of electron-transporting materials. The new compounds were studied in monolayers at the air-water interface, and were further characterized by cyclic voltammetry. The spreading behaviour of long-chain esters of a fluorenylidene malononitrile carboxylic acid was relatively insensitive to the cross-sectional area of the hydrocarbon chain, but was more strongly affected by changes in the polarity of the hydrophilic groups. Conditions for Langmuir-Blodgett deposition of multilayers of two of the new compounds on titanium-coated polyester film were also explored.Key words: monolayers, Langmuir-Blodgett films, fluorene, surfactants. Chem. 67,2136Chem. 67, (1989. Dans le but de prkparer des systbmes de films minces incorporant des monocouches de substances pouvant transporter des Clectrons, on a synthCtisC des dCrivts tensio-actifs qui contiennent des groupements fluorenylidbnes. On a CtudiC les nouveaux composCs dans des monocouches h l'interface air-eau et on les a aussi caractCrisCs par voltamttrie cyclique. La propension B se rtpandre que posskdent les esters en longues chaines d'un acide fluorenylidbne malononitrile carboxylique ne varie pas beaucoup avec des variations de la surface de la section droite de la chaine hydrocarbonte; elle est toutefois plus affectCe par les changements dans la polarit6 des groupements hydrophiles. On a aussi explore les conditions d'effectuer une dCposition de Langmuir-Blodgett de multicouches de deux des nouveaux composCs sur un film de polyester recouvert de titane.