Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 15, Pages 3287-3296Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904718
Keywords
crystal engineering; electrochemistry; photochemistry; porphyrinoids; UV; Vis spectroscopy
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [182849149]
- Graduate School Molecular Science (GSMS)
- Alexander von Humboldt Foundation
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Tetraaryltetrabenzoporphyrins (TATBPs) show, due to their optoelectronic properties, rising potential as dyes in various fields of physical and biomedical sciences. However, unlike in the case of porphyrins, the potential structural diversity of TATBPs has been explored only to little extent, owed mainly to synthetic hurdles. Herein, we prepared a comprehensive library of 30 TATBPs and investigated their fundamental properties. We elucidated structural properties by X-ray crystallography and found explanations for physical properties such as solubility. Fundamental electronic aspects were studied by optical spectroscopy as well as by electrochemistry and brought in context to the stability of the molecules. Finally, we were able to develop a universal synthetic protocol, utilizing a readily established isoindole synthon, which gives TATBPs in high yields, regardless of the nature of the used arylaldehyde and without meticulous chromatographic purifications steps. This work serves as point of orientation for scientists, that aim to utilize these molecules in materials, nanotechnological, and biomedical applications.
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