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

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

doi:10.3390/cryst10010036

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Article number	36
Journal	Crystals
Volume	10
Issue number	1
DOIs	https://doi.org/10.3390/cryst10010036
Publication status	Published - 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

General Chemical Engineering
General Materials Science
Condensed Matter Physics
Inorganic Chemistry

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10.3390/cryst10010036

Cite this

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

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.",

keywords = "Boron-dipyrromethene dye, Halogen bonding, Hirshfeld surface analysis, Polymorphism, Spectroelectrochemistry",

author = "Hawazen Hassanain and Davies, {E. Stephen} and William Lewis and Kays, {Deborah L.} and Champness, {Neil R.}",

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: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

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doi = "10.3390/cryst10010036",

language = "English",

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T2 - Synthesis, structure and electrochemical studies

AU - Hassanain, Hawazen

AU - Davies, E. Stephen

AU - Lewis, William

AU - Kays, Deborah L.

AU - Champness, Neil R.

N1 - 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.

PY - 2020/1/14

Y1 - 2020/1/14

N2 - 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.

AB - 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.

KW - Boron-dipyrromethene dye

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KW - Hirshfeld surface analysis

KW - Polymorphism

KW - Spectroelectrochemistry

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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