Jun 2, 2019
Synthesis, Structural and Optical Properties of Tetrabenzoporphyrin Complexes Bearing Four or Eight Peripheral Phenyl Groups
European Journal of Organic Chemistry
- Volume
- 2019
- Number
- 20
- First page
- 3224
- Last page
- 3235
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1002/ejoc.201900528
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim A series of free-base and phosphorus(V) complexes of tetrabenzoporphyrin (TBP) and some phosphorus(V) porphyrins containing four or eight phenyl groups on the periphery have been synthesized and characterized by X-ray crystallography, electronic absorption, and magnetic circular dichroism (MCD) spectroscopy, together with quantum chemical calculations. All phosphorus TBP and meso-tetraphenyl porphyrin complexes adapted ruffled conformations due to the small P(V) ion, although the Zn(II)TBPs containing eight phenyl (Φ) groups at the so-called β and α positions showed planar and saddled structures in the solid state, due to, respectively, marginal or severe steric hindrance between the neighboring Φ groups. All P(V)TBPs showed the Soret and Q bands beyond 450 and 700 nm, respectively, which are some of the longest wavelengths exhibited by metallated TBPs reported to date. Of the eight Φ group-substituted P(V)TBPs, those substituted at α positions always showed absorption bands at longer wavelengths than those at β positions, which was reproduced by calculated absorption spectra. The Soret band positions of meso-tetraphenylated P(V) species without fused benzo-groups (ca. 430–440 nm) were also some of the longest among metalloporphyrins of this type.
- Link information
- ID information
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- DOI : 10.1002/ejoc.201900528
- ISSN : 1434-193X
- eISSN : 1099-0690
- SCOPUS ID : 85066104782