Synthesis, Photophysical, and Morphological Properties of Azomethine-Persylilated alpha-Cyclodextrin Main-Chain Polyrotaxane
Farcas, A; Resmerita, A; Aubert, PH; Ghosh, I; Cantin, S; Nau, WM
| HERO ID | 3124030 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Synthesis, Photophysical, and Morphological Properties of Azomethine-Persylilated alpha-Cyclodextrin Main-Chain Polyrotaxane |
| Authors | Farcas, A; Resmerita, A; Aubert, PH; Ghosh, I; Cantin, S; Nau, WM |
| Journal | Macromolecular Chemistry and Physics |
| Volume | 216 |
| Issue | 6 |
| Page Numbers | 662-670 |
| Abstract | The synthesis of 2-rotaxane (3â¢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 3â¢TMS-αCD afforded then pyrene-triazole/TMS-αCD PAMs polyrotaxane (4â¢TMS-αCD) azomethine polyrotaxane. The optical, electrochemical, morphological, surface-free energies, as well as transport properties of 3â¢TMS-αCD and its corresponding 4â¢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 (ÏF), significantly longer than that of the starting monomer 3â¢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. Host-guest complexation of azomethine backbones into TMS-αCD cavities leads to improvement of the solubility and better film-forming ability associated with a smoother surface and lower root-mean-square roughness. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| Doi | 10.1002/macp.201400543 |
| Wosid | WOS:000351401600010 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84925069986&doi=10.1002%2fmacp.201400543&partnerID=40&md5=c9c8f671d65f2bc882d998f11c55f10e |
| Is Public | Yes |
| Language Text | English |
| Keyword | azomethine polyrotaxanes; energy bandgaps; fluorescence lifetimes; persylilated -cyclodextrin; surfaces |