Publication: Charge neutral halogen bonding tetradentate-iodotriazole macrocycles capable of anion recognition and sensing in highly competitive aqueous media
Issued Date
2021-11-21
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ISSN
1364548X
13597345
13597345
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2-s2.0-85119959418
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Mahidol University
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SCOPUS
Bibliographic Citation
Chemical Communications. Vol.57, No.90 (2021), 11976-11979
Suggested Citation
Thanthapatra Bunchuay, Kajjana Boonpalit, Andrew Docker, Araya Ruengsuk, Jonggol Tantirungrotechai, Mongkol Sukwattanasinitt, Panida Surawatanawong, Paul D. Beer Charge neutral halogen bonding tetradentate-iodotriazole macrocycles capable of anion recognition and sensing in highly competitive aqueous media. Chemical Communications. Vol.57, No.90 (2021), 11976-11979. doi:10.1039/d1cc05037k Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/76495
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Title
Charge neutral halogen bonding tetradentate-iodotriazole macrocycles capable of anion recognition and sensing in highly competitive aqueous media
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Abstract
A series of neutral tetradentate halogen bonding (XB) macrocycles, comprising of two bis-iodotriazole XB donors were synthesised in 60-70% yields via a stepwise CuAAC-mediated cyclisation strategy. Extensive 1H NMR anion titration experiments reveal halide binding affinities are critically dependent on the substitution pattern of the xylyl spacer unit. The meta-substituted macrocycle remarkably displays cooperative tetradentate XB-halide anion recognition in highly competitive 40% aqueous-organic D2O/acetone-d6 (40 : 60, v/v) solvent mixtures. Integration of para-xylyl and naphthyl spacer units generates extended macrocyclic cavities, capable of selective oxalate recognition. Furthermore, preliminary fluorescence exeperiments reveal dicarboxylate specific sensing can be achieved through monitoring of the naphthylene centred emission. This journal is