Reversible Oxidation of a Nonathia[42]Nonaphyrin(1.1.0.1.1.0.1.1.0) to a 40π Dication Diradicaloid
Abstract A one-pot condensation of bithiophene with thiophene diol under acidic conditions yields 28π, 42π, and 56π expanded porphyrinoids. X-ray crystallographic studies revealed a planar topology for both 28π and 42π macrocycles. Spectroscopic and quantum chemical calculations reveal weak ring current effects, while they undergo reversible two-electron ring oxidation as confirmed by electrochemical studies. Spectroscopic and quantum chemical calculations support a diradicaloid character for the 40π dicationic species.
Authors
- Pragati Shukla (ORCID: https://orcid.org/0000-0002-5849-0853)
- Venkataramanarao G. Anand (ORCID: https://orcid.org/0000-0002-7110-7994)
- Supriyo Santra (ORCID: https://orcid.org/0000-0003-4884-2250)
- Debashree Ghosh (ORCID: https://orcid.org/0000-0003-0726-7878)
- Swati Deswal (ORCID: https://orcid.org/0000-0003-3804-8678)
- Maheswaran Shanmugam (ORCID: https://orcid.org/0000-0002-9012-743X)
- Hosahalli S. Udaya
- Vasudha Sharma (ORCID: https://orcid.org/0000-0002-0323-0771)
- Vijaya Thangaraj
- Bapan Jana
- Nikita Panchmukhi
Institutions
- Indian Institute of Technology Bombay (IN)
- Indian Association for the Cultivation of Science (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-07
- DOI
- https://doi.org/10.1021/acs.orglett.6c02255
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00