A fluorogenic calix[4]pyrrole with a small rigid strap showing different fluorescent responses to anions
- Authors
- Kim, Sung Kuk; Lee, Hong Gyu; Vargas-Zuniga, Gabriela I.; Oh, Ju Hyun; Lynch, Vincent M.; Lee, Min Hee; Sessler, Jonathan L.
- Issue Date
- May-2017
- Publisher
- TAYLOR & FRANCIS LTD
- Keywords
- Anion recognition; sensing; calixpyrroles
- Citation
- SUPRAMOLECULAR CHEMISTRY, v.29, no.9, pp 651 - 657
- Pages
- 7
- Journal Title
- SUPRAMOLECULAR CHEMISTRY
- Volume
- 29
- Number
- 9
- Start Page
- 651
- End Page
- 657
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/8548
- DOI
- 10.1080/10610278.2017.1324624
- ISSN
- 1061-0278
1029-0478
- Abstract
- A strapped calix[4]pyrrole (2) with a fluorogenic pyrene unit linked to the rigid strap via the methylene bridge has been synthesised. It was established by H-1 NMR and fluorescence spectroscopic analyses and isothermal titration calorimetry (ITC) studies that receptor 2 is capable of binding the F-, Cl-, anions in organic media, with high selectivity for F- being observed relative to the other anions. Upon exposure to the F- and HP2O73- the fluorescence of 2 is quenched, an effect ascribed to facilitated PET (photo-induced electron transfer) from the nitrogen atom to the pyrene moiety, which is induced by anion binding. In contrast, the fluorescence of 2 was enhanced upon treatment with the HSO4- anion as the result of the PET inhibition that results from nitrogen atom protonation. A single crystal X-ray structure of the chloride complex of 2 and the H-1 NMR spectral data revealed that the chloride anion is bound to the receptor via aliphatic C-H center dot center dot center dot Cl- hydrogen bonds, as well as N-H center dot center dot center dot Cl- interactions. [GRAPHICS] .
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