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. 2011 Sep 12;17(38):10716-23.
doi: 10.1002/chem.201100691. Epub 2011 Aug 11.

New light on the ring-chain equilibrium of a hydrogen-bonded supramolecular polymer based on a photochromic dithienylethene unit and its energy-transfer properties as a storage material

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New light on the ring-chain equilibrium of a hydrogen-bonded supramolecular polymer based on a photochromic dithienylethene unit and its energy-transfer properties as a storage material

Shao-Lu Li et al. Chemistry. .

Abstract

A novel, bifunctional, quadruple hydrogen-bonding ureido-pyrimidinone (UPy) unit bridged by photochromic dithienylethene (1) has been synthesized, which affords linear assemblies in solution and undergoes concentration-dependent ring-opening polymerization. The two UPy functional groups of 1 can dimerize intramolecularly to form a cyclic monomer with the two thienyl rings fixed in a parallel conformation, which prohibits its photocyclization. We exploited the photochemical reactivity and resonance difference of the linker of the bis-UPy derivative as well as using the more typical (1)H NMR, DOSY, and Ubbelohde viscometry methods to investigate for the first time the ring-chain polymerization mechanism. Moreover, we fabricated a mixed polymer film with a fluorescent dye noncovalently endcapping the linear photochromic assemblies through quadruple hydrogen bonds, which showed nondestructive fluorescent read-out ability for data storage by fluorescence resonance energy transfer (FRET) from the fluorescent dye to the closed form of the diarylethene.

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