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

Research output: Contribution to journalArticlepeer-review

Authors

  • Hawazen Hassanain
  • E. Stephen Davies
  • William Lewis
  • Deborah L. Kays
  • Neil Champness

Colleges, School and Institutes

External organisations

  • University of Nottingham
  • University of Jeddah

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.

Bibliographic 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.

Details

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

Keywords

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