<i>E</i>-Stilbene-Imprinted Cyclic Diphyrin and Its B<sup>III</sup> Complex
Aromaticity in macrocyclic systems arises from the delicate balance of global and local π conjugation. We report a hitherto elusive <i>E</i>-stilbene-imprinted cyclic diphyrin incorporating bis-<i>ortho</i>-phenylene units, enabling four distinct conjugation pathways. The ethylene twist disrupts global conjugation while preserving local aromaticity, introducing a new class of contracted porphyrinoid and inducing non-aromaticity. Complexation with B<sup>III</sup> ions generates asymmetric ring formation within the cavity, transforming non-emissive diphyrin into emissive in solution.
Authors
- Dage Sundholm (ORCID: https://orcid.org/0000-0002-2367-9277)
- Mainak Das (ORCID: https://orcid.org/0000-0003-0244-8215)
- A. Srinivasan (ORCID: https://orcid.org/0000-0001-8467-1538)
- Daniel Blasco (ORCID: https://orcid.org/0000-0001-9291-6187)
- Narayan Ch. Jana (ORCID: https://orcid.org/0000-0002-2849-5784)
- Rampal Vishwakarma
Institutions
- University of Helsinki (FI)
- National Institute of Science Education and Research (IN)
- Universidad de La Rioja (ES)
- Homi Bhabha National Institute (IN)
- University of York (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c01727
- Citations
- 1
- Primary Topic
- Porphyrin and Phthalocyanine Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.52
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Department of Atomic Energy, Government of India
- Academy of Finland
- National Institute of Science Education and Research
- Universidad de La Rioja