Morpholino-substituted BODIPY species: Synthesis, structure and electrochemical studies

Hawazen Hassanain, E. Stephen Davies, William Lewis, Deborah L. Kays*, Neil R. Champness

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Functionalization of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) chromophores at the 2,6-positions with iodo substituents and morpholino-substituted α-methyl groups affords molecules with strong absorbance in the visible spectrum. The effect of such substitution on the solid-state arrangements, absorption, fluorescence and electronic properties of these dye molecules is reported. The spectroscopic and spectroelectrochemical measurements display intense absorptions in the UV-visible spectrum with bathochromic shifts, in comparison to unfunctionalized BODIPY, and a positive shift in redox potentials due to functionalisation of the BODIPY core. Halogen bonds are observed in the solid-state structures of both halogenated BODIPY species, which in one case leads to the formation of an unusual halogen bonded framework.

Original languageEnglish
Article number36
JournalCrystals
Volume10
Issue number1
DOIs
Publication statusPublished - 14 Jan 2020

Bibliographical note

Funding Information:
Acknowledgments: We gratefully acknowledge the support of University of Jeddah (Jeddah, Saudi Arabia) for providing a scholarship for HH. NRC acknowledges financial support from the UK Engineering and Physical Sciences Research Council (EP/S002995/1).

Funding Information:
Funding: This research was funded by the UK Engineering and Physical Sciences Research Council (EP/S002995/1) and support for H.H. from University of Jeddah (Jeddah, Saudi Arabia).

Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Boron-dipyrromethene dye
  • Halogen bonding
  • Hirshfeld surface analysis
  • Polymorphism
  • Spectroelectrochemistry

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Materials Science(all)
  • Condensed Matter Physics
  • Inorganic Chemistry

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