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

  • Marco Lamperti
  • Arianna Maria Giani
  • Angelo Maspero
  • Guglielmo Vesco
  • Alessandro Cimino
  • Roberto Negri
  • Giovanni Battista Giovenzana
  • Giovanni Palmisano
  • Massimo Mella
  • Luca NardoEmail author
ORIGINAL ARTICLE
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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.

Keywords

Perimidines Dihydroperimidines Fluorescence quantum yield Theranostics 

Notes

Funding

This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

Compliance with Ethical Standards

Conflict of Interest

The authors declare that they have no conflict of interest.

Supplementary material

10895_2019_2361_MOESM1_ESM.docx (1 mb)
ESM 1 (DOCX 1059 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Marco Lamperti
    • 1
  • Arianna Maria Giani
    • 2
  • Angelo Maspero
    • 1
  • Guglielmo Vesco
    • 1
  • Alessandro Cimino
    • 1
  • Roberto Negri
    • 2
  • Giovanni Battista Giovenzana
    • 2
  • Giovanni Palmisano
    • 1
  • Massimo Mella
    • 1
  • Luca Nardo
    • 1
    Email author
  1. 1.Dipartimento di Scienza e Alta TecnologiaUniversità degli Studi dell’InsubriaComoItaly
  2. 2.Dipartimento di Scienze del FarmacoUniversità degli Studi del Piemonte Orientale “A. Avogadro”NovaraItaly

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