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Synthesis and Spectroscopic Characterization of 2-(het)Aryl Perimidine Derivatives with Enhanced Fluorescence Quantum Yields

Authors
  • Lamperti, Marco1
  • Giani, Arianna Maria2
  • Maspero, Angelo1
  • Vesco, Guglielmo1
  • Cimino, Alessandro1
  • Negri, Roberto2
  • Giovenzana, Giovanni Battista2
  • Palmisano, Giovanni1
  • Mella, Massimo1
  • Nardo, Luca1
  • 1 Università degli Studi dell’Insubria, Dipartimento di Scienza e Alta Tecnologia, Via Valleggio 11, Como, I-22100, Italy , Como (Italy)
  • 2 Università degli Studi del Piemonte Orientale “A. Avogadro”, Dipartimento di Scienze del Farmaco, Largo Donegani 2/3, Novara, I-28100, Italy , Novara (Italy)
Type
Published Article
Journal
Journal of Fluorescence
Publisher
Springer-Verlag
Publication Date
Mar 12, 2019
Volume
29
Issue
2
Pages
495–504
Identifiers
DOI: 10.1007/s10895-019-02361-9
Source
Springer Nature
Keywords
License
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Abstract

Perimidines are a particularly versatile family of heterocyclic compounds, whose properties are exploited in several applications ranging from industrial to medicinal chemistry. The molecular structure of perimidine incorporates a well-known efficient fluorophore, i.e.: 1,8-diaminonaphthalene. The high fluorescence quantum yield shared by most naphthalene derivatives, has enabled their use as stains for bio-imaging and biophysical characterizations. However, fluorescence is dramatically depressed in perimidine as well as in the few of its derivatives analysed so far to this respect. The use of perimidine-like molecules in life sciences might be notably fostered by enhancement of their fluorescence emission. Even more excitingly, the concomitance of both biologically active moieties and a fluorophore in the same molecular structure virtually discloses application of perimidines as drug compounds in state-of-art theranostics protocols. However, somewhat surprisingly, relatively few attempts were made until now in the direction of increasing the performances of perimidines as fluorescent dyes. In this work we present the synthesis and spectroscopic characterization of four perimidine derivatives designed to this aim, two of which result to be endowed with fluorescence quantum yields comparable to 1,8-diaminonaphthalene. A rationalization for such improved behaviour has been attempted employing TD-DFT calculations, which have unravelled the interrelations among bond structure, lone pair conjugation, local electron density changes and fluorescence quantum yield.

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