Synthesis and solvent sorption characteristics of new types of tartaric acid, lactic acid and TADDOL derived receptor compounds

Abstract

Based on a modular design strategy, three new types of tartaric acid, lactic acid and TADDOL derived compounds featuring a linear shaped central backbone and terminally attached functional units corresponding to the above substance classes have been developed. This has led to the synthesis of the compounds 1a–6a (tartaric acid derivatives), 7a–11a (lactic acid derivatives) and 1c–6c (TADDOL derivatives). Preparation of the tartaric acid derivatives involved Pd-catalysed cross-coupling reactions followed by transacetalisation and hydrolysis of the corresponding esters in the final step of the synthetic routes. The derivatives of lactic acid have been prepared on a similar reaction sequence but with the use of lactic esters. The TADDOL derivatives were obtained by Grignard reaction between phenylmagnesium bromide and tartaric esters. Optical rotation data are specified for each compound including intermediates. Organic vapour sorption behaviour of selected compounds coated as solid films on the quartz crystal of a QCM device has been studied. Significant differences in the affinities towards organic solvent vapours are observed. They both depend on structural properties of the respective receptor solvent molecules and solvent polarity as well, showing developmental possibility in the application of vapour sensing.