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)


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
Issue number1
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.


  • 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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