Porphyrinoids, a unique platform for exploring excited-state aromaticity

Jinseok Kim, Juwon Oh, Atsuhiro Osuka, Dongho Kim

Research output: Contribution to journalReview articlepeer-review

1 Citation (Scopus)

Abstract

Recently, Baird (anti)aromaticity has been referred to as a description of excited-state (anti)aromaticity. With the term of Baird's rule, recent studies have intensively verified that the Hückel aromatic [4n + 2]π (or antiaromatic [4n]π) molecules in the ground state are reversed to give Baird aromatic [4n]π (or Baird antiaromatic [4n + 2]π) molecules in the excited states. Since the Hückel (anti)aromaticity has great influence on the molecular properties and reaction mechanisms, the Baird (anti)aromaticity has been expected to act as a dominant factor in governing excited-state properties and processes, which has attracted intensive scientific investigations for the verification of the concept of reversed aromaticity in the excited states. In this scientific endeavor, porphyrinoids have recently played leading roles in the demonstration of the aromaticity reversal in the excited states and its conceptual development. The distinct structural and electronic nature of porphyhrinoids depending on their (anti)aromaticity allow the direct observation of excited-state aromaticity reversal, Baird's rule. The explicit experimental demonstration with porphyrinoids has contributed greatly to its conceptual development and application in novel functional organic materials. Based on the significant role of porphyrinoids in the field of excited-state aromaticity, this review provides an overview of the experimental verification of the reversal concept of excited-state aromaticity by porphyrinoids and the recent progress on its conceptual application in novel functional molecules.

Original languageEnglish
Pages (from-to)268-272
Number of pages5
JournalChemical Society reviews
Volume51
Issue number1
DOIs
Publication statusPublished - 2022

Bibliographical note

Funding Information:
The work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2021R1A2C300630811 and 2021R1A6A1A03039503). The work was also supported by the Soonchunhyang University Research Fund.

Publisher Copyright:
© 2021 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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