Meso-Nitromethyl-Substituted BODIPYs – A new type of water switchable fluorogenic dyes useful for further core modifications. (February 2018)

• Record Type: Journal Article
• Authors: Didukh, Natalia O.; Yakubovskyi, Viktor P.; Zatsikha, Yuriy V.; Nemykin, Victor N.; Kovtun, Yuriy P.
• Is Part Of: Dyes and pigments. Volume 149(2018)
• Page Start: 774
• Page End: 782
• Publication Date: 2018-02
• Subjects: BODIPY -- UV-Vis spectra -- Fluorophore -- Functionalization -- DFT-PCM and TDDFT-PCM calculations; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2017.11.037
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A two-step synthetic pathway for direct introduction of the nitromethyl functional group at the meso -position of BODIPY core was explored using a number of meso -unsubstituted BODIPY platforms. Spectral properties of the resulting meso -nitromethyl containing BODIPYs was found to be sensitive to the pH change as well as to the presence of water in organic solvents. Meso -nitromethyl group can be used for further modification of the BODIPY core via reduction or condensation reactions. DFT-PCM and TDDFT-PCM calculations correlate well with the experimental data and explain the observed spectral properties. Graphical abstract: Highlights: Two-step synthetic pathway for direct introduction of the nitromethyl group at the meso -position of BODIPY was developed. Spectral properties of nitro- and aci- tautomers were studied. DFT-PCM and TDDFT-PCM calculations were conducted on the meso -nitromethyl BODIPY systems.