Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 38, Pages 10716-10723Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100691
Keywords
energy transfer; photochromism; polymers; ring-opening polymerization; supramolecular chemistry
Categories
Funding
- National Natural Science Foundation of China [20932004, 21072093]
- National Basic Research Program of China [2007CB925103, 2011CB808600]
- Program for New Century Excellent Talents in University [NCET-07-0425]
- Ministry of Education of China [20090091110017]
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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 H-1 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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