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Synthesis and photoisomerization study of new aza-crown macrocyclic tweezer tethered through an azobenzene linker: the first report on supramolecular interaction of azobenzene moiety with C60

Ghanbari, B ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1016/j.molstruc.2017.05.063
  3. Abstract:
  4. In the present communication, three bimacrocyclic tweezers linked through azobenzene moiety, Ln (n = 1–3) were synthesized in a multistep route and characterized by x-ray crystallography, IR, 1H and 13C NMR, UV–vis spectroscopy as well as CHN microanalysis. UV–visible spectroscopy established that the irradiation of L1 and L3 with UV light promoted the trans to cis isomerization. Irradiating the reaction mixtures with Hg lamp, significant supramolecular interactions between L1 and L3 with C60 were also found in terms of the association constants calculated by UV–visible spectroscopy, denoting on more pronounced interaction with C60 that in the absence of UV light. The molecular structures of L1-L3 calculated by using DFT method suggested a novel unprecedented interaction between the HOMO's of azobenzene moiety on the tweezer instead of the aromatic groups with C60. © 2017 Elsevier B.V
  5. Keywords:
  6. C60 ; Macrocyclic tweezer ; Association reactions ; Azobenzene ; Crystallography ; Infrared spectrophotometers ; Supramolecular chemistry ; Association constant ; Azobenzene moiety ; Cis-trans ; Macrocyclics ; Supramolecular ; Supramolecular interactions ; VIS spectroscopy ; Visible spectroscopy ; X ray crystallography
  7. Source: Journal of Molecular Structure ; Volume 1144 , 2017 , Pages 360-369 ; 00222860 (ISSN)
  8. URL: https://www.sciencedirect.com/science/article/abs/pii/S0022286017306725