Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies
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 a...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-01-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/1/36 |
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| author | Hawazen Hassanain E. Stephen Davies William Lewis Deborah L. Kays Neil R. Champness |
| author_facet | Hawazen Hassanain E. Stephen Davies William Lewis Deborah L. Kays Neil R. Champness |
| author_sort | Hawazen Hassanain |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-14T03:28:07Z |
| format | Article |
| id | doaj.art-6202c39832a74f5f80817b7fb19515ec |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-14T03:28:07Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-6202c39832a74f5f80817b7fb19515ec2022-12-22T02:15:04ZengMDPI AGCrystals2073-43522020-01-011013610.3390/cryst10010036cryst10010036Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical StudiesHawazen Hassanain0E. Stephen Davies1William Lewis2Deborah L. Kays3Neil R. Champness4School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UKSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UKSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UKSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UKSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UKFunctionalization 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.https://www.mdpi.com/2073-4352/10/1/36boron-dipyrromethene dyehalogen bondingpolymorphismhirshfeld surface analysisspectroelectrochemistry |
| spellingShingle | Hawazen Hassanain E. Stephen Davies William Lewis Deborah L. Kays Neil R. Champness Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies Crystals boron-dipyrromethene dye halogen bonding polymorphism hirshfeld surface analysis spectroelectrochemistry |
| title | Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies |
| title_full | Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies |
| title_fullStr | Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies |
| title_full_unstemmed | Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies |
| title_short | Morpholino-Substituted BODIPY Species: Synthesis, Structure and Electrochemical Studies |
| title_sort | morpholino substituted bodipy species synthesis structure and electrochemical studies |
| topic | boron-dipyrromethene dye halogen bonding polymorphism hirshfeld surface analysis spectroelectrochemistry |
| url | https://www.mdpi.com/2073-4352/10/1/36 |
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