Synthesis of hyper-cross-linked microporous poly(phenylacetylene)s having aldehyde and other groups and their chemisorption and physisorption ability

The chain-growth homopolymerization of 3,5-diethynylbenzaldehyde proceeding through the transformation of the ethynyl groups of the monomer yields hyper-cross-linked poly(3,5-diethynylbenzaldehyde), P(DEBA), with a high content of carbaldehyde groups (6.5 mmol/g) and specific surface of about 900 m(2)/g. The covalent structure of P(DEBA) consists of polyene (polyacetylene) main chains cross-linked with 5-formyl-1,3-phenylene links. P(DEBA) selectively and reversibly chemisorbs alcohols and primary amines (capacity up to 350 mg/g) through binding these solutes in the form of acetal and Schiff base type segments, respectively. The condensation of P(DEBA) carbaldehyde groups with amino groups of ethylenediamine (EDA) gives microporous P(DEBA)/EDA2 extensively decorated with base NH2 groups. P(DEBA)/EDA2 is effective for physisorption of ibuprofen solute (capacity, 1130 mg/g) and CO2 gas (capacity, 360 mg/g, 7 bar, 273 K) and is active as a heterogeneous catalyst of aldol condensation of n-heptanal with benzaldehyde to jasminaldehyde.