Synthetically Induced 1 -> 4-C Branching Motif - An Access Towards Dense Urethane Connecting Dendritic Scaffolds and Application in Nuclear Track Detection

CHEMISTRYSELECT(2019)

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Abstract
A series of dumbbell-shaped urethane connecting polyoleifinic dendrimers, are synthesized from commercial AB(2) monomer through the concept of post-generative synthetic induction of novel 1 -> 4-C branching motif in divergent and convergent growth methodology using carbamoyl chloride reactivity. A synthetic protocol is conducted through the iterative process of O-carbamoyl-allylation of hydroxyls followed by Upjohn dihydroxylation of the allylic double bonds, leading to protection/deprotection free divergent pathway. In parallel, convergent growth route gains dendrimers in relatively good yields. Also, the process of O-carbonyloxy-allylation of [G-1] polyol affords urethane-carbonate framework providing access to 1 -> 2-C branching further. Incorporation of current branching motif results in dendritic scaffold with dense periphery at lower generations itself. Free radical cast polymerization of [G-0.5] dendrimer with allyl diglycol carbonate (ADC) produces thermoset polymer films, showing good sensitivity and ability to permanently record nuclear tracks.
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Key words
1 -> 4-C branching motifs,O-carbamoyl-allylation,O-carbonyloxy-allylation,free radical polymerization,nuclear track detectors,urethane dendrimer
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