Abstract
Donor–acceptor Stenhouse adducts (DASAs) are gaining attention from organic and material chemists due to their visible light-stimulated photochromic properties. In this report, we present a facile method for grafting coloured triene on polycarbonate surface, without involving any pre-treatments like plasma activation, etc. The chemoselectivity of carbonate with a primary amine and Meldrum's activated furan (MAF) with polymer bound secondary amine has been exploited to graft photoswitchable DASA on the polymer surface. Primary, secondary and tertiary amine-functionalized polycarbonate surfaces have been prepared to evaluate the reactivity of amine with MAF.
Highlights
Apart from solid-phase organic synthesis, polymer functionalization plays a crucial role in the discovery of new bioactive surfaces for biomaterial and tissue engineering applications [1]
We report our observation for selective formation of Donor–acceptor Stenhouse adducts (DASAs) on polycarbonate (PC) bound secondary amines
PC appears to be a suitable material of choice for biotechnological applications due to its (i) availability as porous membranes with controllable pore size [13], (ii) micro thermoformability that is useful for generating three-dimensional microgeometries and vessel-like structures [14] and (iii) facile surface chemistry [15]
Summary
Apart from solid-phase organic synthesis, polymer functionalization plays a crucial role in the discovery of new bioactive surfaces for biomaterial and tissue engineering applications [1]. Light-induced isomerization phenomenon is mostly observed with high-energy photons in UV range [6]. In 2014, Read de Alaniz and co-workers [10] introduced donor–acceptor Stenhouse adducts (DASAs) as potential new candidates for visible light-induced photochromism. We report our observation for selective formation of DASA on polycarbonate (PC) bound secondary amines. It is a facile method for grafting photosensitive trienes on transparent PC surface, by making use of chemoselective reaction of a primary amine with carbonate and secondary amine with MAF
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