Structurally Diverse Triphenylamine[<i>n</i>]arenes with Room-Temperature Phosphorescence

We present the design and synthesis of a series of triphenylamine[<i>n</i>]arenes. The incorporation of alkyl and aryl aldehydes together with paraformaldehyde introduces multiple reactive sites into the macrocyclic framework. The methylenes can be oxidized to carbonyls using 3,5-dichloro-2,6-dicyano-1,4-benzoquinone (DDQ), which exhibits significantly enhanced fluorescence and room-temperature phosphorescence (RTP). This investigation provides an efficient strategy for the synthesis of RTP-active macrocyclic arenes, thereby broadening the scope of macrocyclic arene chemistry and advancing their application in luminescent materials.

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Publication Details

Journal
Organic Letters
Published
2025-06-16
DOI
https://doi.org/10.1021/acs.orglett.5c01973
Citations
6
Primary Topic
Luminescence and Fluorescent Materials
Type
article
Field-Weighted Citation Impact
3.11

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article

Structurally Diverse Triphenylamine[n]arenes with Room-Temperature Phosphorescence

Shifa Zhu, Manfei Zhou, Ruyi Sun, Min Qi et al.
6 citations
Organic Letters
Luminescence and Fluorescent Materials
3.11
article

Structurally Diverse Triphenylamine[n]arenes with Room-Temperature Phosphorescence

Shifa Zhu, Manfei Zhou, Ruyi Sun, Min Qi, Da Ma, Xueliang Shi, Guang‐Qiang Yin, Lu Wang, Lijun Mao, Sanhanut Jongaksorn
article en
6 citations

Abstract

We present the design and synthesis of a series of triphenylamine[<i>n</i>]arenes. The incorporation of alkyl and aryl aldehydes together with paraformaldehyde introduces multiple reactive sites into the macrocyclic framework. The methylenes can be oxidized to carbonyls using 3,5-dichloro-2,6-dicyano-1,4-benzoquinone (DDQ), which exhibits significantly enhanced fluorescence and room-temperature phosphorescence (RTP). This investigation provides an efficient strategy for the synthesis of RTP-active macrocyclic arenes, thereby broadening the scope of macrocyclic arene chemistry and advancing their application in luminescent materials.

Organic LettersVol. 27(25)
Chinese Academy of Sciences (CN), Advanced Energy Materials (United States) (US), Ningbo Institute of Industrial Technology (CN), East China Normal University (CN), Taizhou University (CN)
Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 8%
Luminescence and Fluorescent Materials
3.11
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