Sequential N-Alkylations of Tetrabenzotetraaza[8]circulene as a Tool To Tune Its Optical Properties

Fengkun Chen, Yong Seok Hong, Dongho Kim, Takayuki Tanaka, Atsuhiro Osuka

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Sequential N-alkylations of tetrabenzotetraaza[8]circulene provided mono-, di-, tri, and tetra-N-alkylated products in a controlled manner. Curiously, only opp isomer was obtained as a di-N-alkylated product. Upon increase of the N-alkyl groups, the absorption and emission spectra exhibit continuous red-shifts, and the excited-state lifetimes become shortened, probably because of increased steric congestion at the nitrogen atoms that causes the central core to deviate from planarity. Mixed N-substituted [8]circulenes have been also prepared.

Original languageEnglish
Pages (from-to)1048-1051
Number of pages4
JournalChemPlusChem
Volume82
Issue number7
DOIs
Publication statusPublished - 2017 Aug 1

Bibliographical note

Funding Information:
The work at Kyoto was supported by Grants-in-Aid from JSPS KAKENHI Grant Numbers (25220822, 26810021 and JP16H00909). The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183). The authors thank Prof. Dr. Hiromitsu Maeda and Dr. Yuya Bando (Ritsumeikan University) for MALDI-TOF MS measurement.

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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