- Title
- Electronic structure and NH-tautomerism of a novel metal-free phenanthroline-annelated phthalocyanine
- Creator
- Martynov, Alexander G, Mack, John, Ngoy, Bokolombe P, Nyokong, Tebello, Gorbunova, Yulia G, Tsivadze, Aslan Yu
- Subject
- To be catalogued
- Date
- 2017
- Type
- text
- Type
- article
- Identifier
- http://hdl.handle.net/10962/239643
- Identifier
- vital:50751
- Identifier
- xlink:href="https://doi.org/10.1016/j.dyepig.2017.01.072"
- Description
- A novel low-symmetry A3B-type phthalocyanine annelated with a pyrazino[2,3-f]phenanthroline ring system and substituted with six solubilizing diisopropylphenoxy-groups (1) was synthesized by metalfree DBU-promoted cross-condensation of diiminoisoindolines derived from 4,5- bis(diisopropylphenoxy)phthalonitrile and pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile. The use of these particular precursors affords A3B phthalocyanine in 15% yield, while cross-condensation of the corresponding dinitriles yields only trace amounts of the target compound. Comparative studies of the A3B-type phthalocyanine and its symmetrical octa(diisopropylphenoxy)-substituted counterpart 2 reveal striking differences in the Q band regions of their UVevisible absorption (UVeVis) spectra, which could be readily rationalized through a comparison with calculated TD-DFT spectra. Since 1 can have two NH-tautomers with equivalent and non-equivalent NH-groups, and DFT calculations predict that the former tautomer is only 2.3 kcal/mol more stable than the latter one, a comprehensive analysis of 13C NMR spectra was carried out through the application of 1 He13C HMBC and HSQC techniques. It demonstrated that only the tautomer with equivalent NH-groups is present in solution.
- Format
- computer, online resource, application/pdf, 1 online resource (11 pages), pdf
- Publisher
- Elsevier
- Language
- English
- Relation
- Dyes and Pigments, Martynov, A.G., Mack, J., Ngoy, B.P., Nyokong, T., Gorbunova, Y.G. and Tsivadze, A.Y., 2017. Electronic structure and NH-tautomerism of a novel metal-free phenanthroline-annelated phthalocyanine. Dyes and Pigments, 140, pp.469-479, Dyes and Pigments volume 140 p. 469 2017 1873-3743
- Rights
- Publisher
- Rights
- Use of this resource is governed by the terms and conditions of the Elsevier Terms and Conditions Statement (https://www.elsevier.com/legal/elsevier-website-terms-and-conditions)
- Rights
- Closed Access
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Collections
Mack, John (Associate Prof)
Nyokong, Tebello (Distinguished Professor)
RU DST/NRF SARChI for Medicinal Chemistry and Nanotechnology
RU Department of Chemistry
SDG 03. Good Health and Well-Being
| Thumbnail | File | Description | Size | Format | |||
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| View Details | SOURCE1 | Electronic structure and NH-tautomerism.pdf | 705 KB | Adobe Acrobat PDF | View Details |