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- Title
Synthesis, Photophysical, and Morphological Properties of Azomethine-Persylilated α-Cyclodextrin Main-Chain Polyrotaxane.
- Authors
Farcas, Aurica; Resmerita, Ana‐Maria; Aubert, Pierre‐Henri; Ghosh, Indrajit; Cantin, Sophie; Nau, Werner M.
- Abstract
The synthesis of 2-rotaxane (3•TMS-αCD) through a condensation reaction between 3,5-diamino-1,2,4-triazole encapsulated into hexakis(2,3,6-trimethylsilyl) α-cyclodextrin cavity (TMS-αCD ) and 1-pyrenecarboxaldehyde is reported. The oxidative coupling of 3•TMS-αCD afforded then pyrene-triazole/TMS-αCD PAMs polyrotaxane (4•TMS-αCD) azomethine polyrotaxane. The optical, electrochemical, morphological, surface-free energies, as well as transport properties of 3•TMS-αCD and its corresponding 4•TMS-αCD polyrotaxane have been investigated and compared with those of the reference polymer pyrene-triazole azomethine. The polyrotaxane is soluble in toluene/dimethylformamide (DMF) 1:1, v/v, mixture and displays useful levels of thermal stability and higher fluorescence quantum yield ( ΦPL) in DMF solutions. ΦPL improvement is further reflected in the fluorescence lifetime ( τF), significantly longer than that of the starting monomer 3•TMS-αCD (7.8 vs 0.89 ns). In addition, a smoother surface with the smaller grains uniformly distributed on the surface, as well as lower surface-free energy, combined with energy gap (3.32 vs 3.76 eV) represent noticeable advantages of azomethine backbones encapsulation by TMS-αCD.
- Subjects
ROTAXANES synthesis; CYCLIC compounds synthesis; CYCLODEXTRINS synthesis; CHEMICAL synthesis; SCHIFF bases
- Publication
Macromolecular Chemistry & Physics, 2015, Vol 216, Issue 6, p662
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.201400543