Interaction of aromatic compounds and anions with naphthylimide-dansylamide fluorescent dyad: Experimental evidence of aryl C-H…π and aryl C-H…anion contacts and DFT calculations

Miguel Ángel Claudio-Catalán; Felipe Medrano; Hugo Tlahuext; Nadia Alejandra Rodríguez-Uribe; Carolina Godoy-Alcántar

doi:10.1016/j.saa.2019.117553

Interaction of aromatic compounds and anions with naphthylimide-dansylamide fluorescent dyad: Experimental evidence of aryl C-H…π and aryl C-H…anion contacts and DFT calculations

Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 5:226:117553. doi: 10.1016/j.saa.2019.117553. Epub 2019 Oct 10.

Authors

Miguel Ángel Claudio-Catalán¹, Felipe Medrano², Hugo Tlahuext³, Nadia Alejandra Rodríguez-Uribe³, Carolina Godoy-Alcántar⁴

Affiliations

¹ Departamento de Ciencias Químico-Biológicas, Instituto de Ciencias Biomédicas, Universidad Autónoma de Ciudad Juárez, Avenida Plutarco Elías Calles, 1210, Fovissste Chamizal, Ciudad Juárez, Chihuahua, Mexico.
² Departamento de Ciencias Químico-Biológicas, Universidad de Sonora, Rosales y Luis Encinas s/n, Hermosillo, Sonora, 83000, Mexico.
³ Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Col. Chamilpa, Cuernavaca, Morelos, 62209, Mexico.
⁴ Centro de Investigaciones Químicas, IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Col. Chamilpa, Cuernavaca, Morelos, 62209, Mexico. Electronic address: cga@uaem.mx.

PMID: 31634713
DOI: 10.1016/j.saa.2019.117553

Abstract

In this work the interaction of halide anions and simple aromatic compounds with a bichromophoric fluorescent dyad derived from 1,8-naphthalimide (NAPIM) and 5-(dimethylamino)naphthalene-1-sulfonyl (DANS) was studied using electronic spectroscopy, ¹H, and ¹⁹F NMR spectroscopy and quantum chemistry modeling (b3lyp/def2-TZVP). The NAPIM-DANS dyad interacts with electron-rich guests with binding constants in the range of 6×10³ to 8×10³M^-1 in CHCl₃. The formed complexes are stabilized through aryl C-H … anion and aryl C-H … π interactions.

Keywords: Aryl C–H…anion; Aryl C–H…π; Density functional theory; Dyad; Naphthylimide-dansylamide.