Synthesis and characterization of vinylimidazolium salts: Solution state study to realize the influence of different anions

Paladugu, S and Arpan, S and Arruri, S and G, Prabusankar (2012) Synthesis and characterization of vinylimidazolium salts: Solution state study to realize the influence of different anions. Journal of Molecular Structure, 1024. pp. 170-175. ISSN 0022-2860

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Abstract

New vinylimidazolium salts, [9,10-bis{(N-vinylimidazolium)methyl}anthracene] bistetrafluoroborate (2) and [9,10-bis{(N-vinylimidazolium)methyl}anthracene] bishexafluorophosphate (3) have been prepared by the N alkylation of 9,10-bis(chloromethyl)anthracene with 1-vinylimidazole in 1,4-dioxane at 70 °C followed by the anion exchange reaction between [9,10-bis{(N-vinylimidazolium)methyl}anthracene] dichloride (1) and ammonium salt of tetrafluoroborate (for 2) or hexafluorophosphate (for 3). The interaction of tribromide anion with 1–3 has been studied with the help of 1H NMR and fluorescence spectra. Notably, the tribromide anion exhibits very strong fluorescent quenching effects towards 2 than 1 and 3. Similarly, 2 shows very strong fluorescent quenching effect in the presence of tribromide anion compare to bromide anion. Moreover the proton of imidazolium cation, Nsingle bondCHsingle bondN in 2 undergoes considerable downfield shift in the presence of tribromide anion, while the vinyl group depicts strong upfield shift due to the possible interaction of tribromide with vinylimidazolium unit.

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IITH Creators:
IITH CreatorsORCiD
G, Prabusankarhttp://orcid.org/0000-0003-1772-135X
Item Type: Article
Additional Information: Supplementary data (1H NMR, 13C NMR, 31P NMR, FT-IR, single crystal X-ray structure, and Fluorescence spectra) associated with this article can be found, in the online version.
Uncontrolled Keywords: Anthracene; 1-Vinylimidazole; Tribromide anion; N-heterocyclic carbene; Imidazolium salts
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Mr. Siva Shankar K
Date Deposited: 24 Sep 2014 05:03
Last Modified: 12 Sep 2017 06:35
URI: http://raiith.iith.ac.in/id/eprint/55
Publisher URL: https://doi.org/10.1016/j.molstruc.2012.05.030
OA policy: http://www.sherpa.ac.uk/romeo/issn/0022-2860/
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