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Open AccessArticle

Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies

1
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
2
Department of Chemistry, College of Science, University of Jeddah, P.O. BOX 34, Jeddah 21959, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(1), 36; https://doi.org/10.3390/cryst10010036
Received: 23 December 2019 / Revised: 7 January 2020 / Accepted: 11 January 2020 / Published: 14 January 2020
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. View Full-Text
Keywords: boron-dipyrromethene dye; halogen bonding; polymorphism; Hirshfeld surface analysis; spectroelectrochemistry boron-dipyrromethene dye; halogen bonding; polymorphism; Hirshfeld surface analysis; spectroelectrochemistry
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Hassanain, H.; Davies, E.S.; Lewis, W.; Kays, D.L.; Champness, N.R. Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies. Crystals 2020, 10, 36.

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