Photoinduced electron transfer in N,N-bis(pyridylmethyl)naphthalenediimides: study of their potential as pH chemosensors

The change in fluorescent properties of a series of N,N-bis(pyridylmethyl)naphthalenediimides (BIPy-NDIs) as function of pH were investigated. The naphthalenediimide dyes displayed OFF-ON pH sensing properties owing to photoinduced electron transfer in the pH range from 1.7 to 4.1. The fluorescence...

Full description

Saved in:
Bibliographic Details
Published in:Supramolecular chemistry 2017-01, Vol.29 (1), p.32-39
Main Authors: Martínez-Quiroz, Marisela, Ochoa-Terán, Adrián, Pina-Luis, Georgina, Santacruz Ortega, Hisila
Format: Article
Language:English
Subjects:
N,N′-bis(pyridylmethyl)naphthalenediimides
PET
pH chemosensor
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The change in fluorescent properties of a series of N,N-bis(pyridylmethyl)naphthalenediimides (BIPy-NDIs) as function of pH were investigated. The naphthalenediimide dyes displayed OFF-ON pH sensing properties owing to photoinduced electron transfer in the pH range from 1.7 to 4.1. The fluorescence enhancement of the chemosensors studied is based on the hindering of photoinduced energy-electron transfer (PET) from pyridine ring to the naphthalene fluorophore by protonation. Moreover, using density functional theory theoretical calculations of molecular orbitals, it was verified that protonation nitrogen atom in pyridine ring inhibits the PET process. The best selective response for monitoring pH in the presence of different metal ions, was exhibited by BIPy-NDI 1B. In addition, 1B was applied for determination of pH in real samples of commercial vinegars. The results were consistent with those obtained by glass electrode method, indicating that the new probe could be a practical pH indicator in strongly acidic conditions.
ISSN:1061-0278
1029-0478
DOI:10.1080/10610278.2016.1162905