Control and Switching of Aromaticity in Various All-Aza-Expanded Porphyrins: Spectroscopic and Theoretical Analyses

Young Mo Sung, Juwon Oh, Won Young Cha, Woojae Kim, Jong Min Lim, Min Chul Yoon, Dongho Kim

Research output: Contribution to journalReview articlepeer-review

127 Citations (Scopus)


Modification of aromaticity is regarded as one of the most interesting and important research topics in the field of physical organic chemistry. Particularly, porphyrins and their analogues (porphyrinoids) are attractive molecules for exploring various types of aromaticity because most porphyrinoids exhibit circular conjugation pathways in their macrocyclic rings with various molecular structures. Aromaticity in porphyrinoids is significantly affected by structural modification, redox chemistry, NH tautomerization, and electronic states (singlet and triplet excited states). Conversely, aromaticity significantly affects the spectroscopic properties and chemical reactivities of porphyrinoids. In this context, considerable efforts have been devoted to understanding and controlling the aromaticity and antiaromaticity of porphyrinoids. Thus, a series of porphyrinoids are in the limelight, being expected to shed light on this field because they have some advantages to demonstrate the switching of aromaticity; it is possible to control the aromaticity by lowering the temperature, adding and removing the protons of expanded porphyrins, changing the chemical environment, and switching the electronic states (triplet and singlet excited states) by photoexcitation. In this regard, this Review describes the control of aromaticity in various expanded porphyrins from the spectroscopic point of view with assistance from theoretical calculations.

Original languageEnglish
Pages (from-to)2257-2312
Number of pages56
JournalChemical Reviews
Issue number4
Publication statusPublished - 2017 Feb 22

Bibliographical note

Funding Information:
supported by the Global Research Laboratory (GRL, 2013K1A1A2A0205183) Program funded by the Ministry of Education, Science and Technology (MEST) of Korea. The research topic in section 5 was supported by Samsung Science and Technology Foundation under Project no. SSTF-BA1402-10. The quantum calculations were performed using the supercomputing resources of the Korea Institute of Science and Technology Information (KISTI).

Publisher Copyright:
© 2016 American Chemical Society.

All Science Journal Classification (ASJC) codes

  • Chemistry(all)


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