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Bis‐ (Dibenzothiophene) Embedded Hexaphyrins: Synthesis, Structure and Properties
Author(s) -
Sinha Avisikta,
Kumar Ankit,
Ravikanth Mangalampalli
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100157
Subject(s) - dibenzothiophene , chemistry , cyclohexane , ring (chemistry) , absorption (acoustics) , aryl , absorption spectroscopy , density functional theory , medicinal chemistry , combinatorial chemistry , organic chemistry , computational chemistry , catalysis , materials science , alkyl , physics , quantum mechanics , composite material
We report our successful synthesis of two stable bis ‐(dibenzothiophene) embedded hexaphyrins by condensing one equivalent of dibenzothiophene based tripyrrane with one equivalent of aryl aldehydes such as pentafluorobenzaldehyde and p ‐nitrobenzaldehyde under acid catalysed conditions. The blue coloured dibenzothiophene (DBT) embedded hexaphyrins were characterised by various spectroscopic techniques. The X‐ray structure obtained for one of the DBT embedded hexaphyrins showed the unusual unique chair like conformation of the macrocycle which is similar to cyclohexane ring. The X‐ray crystallographic analysis was further supported by DFT studies. The NMR, absorption and DFT studies indicated the non‐aromatic nature of the macrocycles. TD‐DFT calculations successfully reproduced experimentally observed absorption spectra of bis ‐(dibenzothiophene) embedded hexaphyrins.