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Yu S, Plunkett W, Kim M, et al. Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol. J Org Chem. 2013;78(24):12671-80doi: 10.1021/jo402277p.
Yu, S., Plunkett, W., Kim, M., Wu, E., Sabat, M., & Pu, L. (2013). Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol. The Journal of organic chemistry, 78(24), 12671-80. https://doi.org/10.1021/jo402277p
Yu, Shanshan, et al. "Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol." The Journal of organic chemistry vol. 78,24 (2013): 12671-80. doi: https://doi.org/10.1021/jo402277p
Yu S, Plunkett W, Kim M, Wu E, Sabat M, Pu L. Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol. J Org Chem. 2013 Dec 20;78(24):12671-80. doi: 10.1021/jo402277p. Epub 2013 Dec 06. PMID: 24283254.
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J Org Chem. 2013 Dec 20;78(24):12671-80. doi: 10.1021/jo402277p. Epub 2013 Dec 06.

Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol.

The Journal of organic chemistry

Shanshan Yu, Winston Plunkett, Michael Kim, Elaine Wu, Michal Sabat, Lin Pu

Affiliations

  1. Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904-4319, United States.

PMID: 24283254 DOI: 10.1021/jo402277p

Abstract

The fluorescent responses of 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol toward a variety of amines have been studied. It was found that the aliphatic primary 1,2- and 1,5-diamines can greatly enhance the fluorescence of this compound, but under the same conditions, primary, secondary, and tertiary monoamines cannot turn on the fluorescence of this compound. In addition, this compound was shown to be an enantioselective and diastereoselective fluorescent sensor for chiral diamines. UV absorption and NMR spectroscopic methods have been used to study the interaction of the sensor with amines. These studies have demonstrated that the intramolecular OH···O═C hydrogen bonding of the sensor is important for both the reactivity of its trifluoroacetyl group with the amines and its fluorescent responses. The interaction of both of the two amine groups of a diamine molecule with the sensor is essential for the observed fluorescent sensitivity and selectivity.

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