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Title: Synthesis, Structure, and Optical Properties of Di-m-benzihexaphyrins ( and Di-m-benziheptaphyrins ( Blackening of m-Phenylene-Linked Dicarbaporphyrinoids by Simple π-Expansion
Authors: Sulfikarali, T
Ajay, J
Suresh, C H
Bijina, P V
Gokulnath, S
Keywords: Di-m-benzihexaphyrins
Issue Date: 19-Jun-2020
Publisher: ACS Publications
Citation: The Journal of Organic Chemistry;85(12):8021-8028
Abstract: Acid-catalyzed condensation of a newly prepared di-mbenzipentapyrrane with appropriate mono- and diheterocyclic dialcohols selectively produced stable di-m-benzihexaphyrins and di-m-benziheptaphyrins with only two meso-carbon bridges. Single-crystal X-ray diffraction analyses reveal planar conformation with slight distortion of bridged phenylene rings. Despite the presence of m-phenylene units interrupting the global delocalization, the presence of bithiophene units in di-mbenziheptaphyrins 3a−b exhibits altered optical features covering the entire visible region (ca. 250−720 nm), exhibiting a black dye property as a “metalfree” porphyrinoid.
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