Ortho-Substituted Aryldiazonium Design for the Defect Configuration-Controlled Photoluminescent Functionalization of Chiral Single-Walled Carbon Nanotubes

Boda Yu, Sadahito Naka, Haruka Aoki, Koichiro Kato, Daiki Yamashita, Shun Fujii, Yuichiro K. Kato, Tsuyohiko Fujigaya, Tomohiro Shiraki

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Defect functionalization of single-walled carbon nanotubes (SWCNTs) by chemical modification is a promising strategy for near-infrared photoluminescence (NIR PL) generation at >1000 nm, which has advanced telecom and bio/medical applications. The covalent attachment of molecular reagents generates sp3-carbon defects in the sp2-carbon lattice of SWCNTs with bright red-shifted PL generation. Although the positional difference between proximal sp3-carbon defects, labeled as the defect binding configuration, can dominate NIR PL properties, the defect arrangement chemistry remains unexplored. Here, aryldiazonium reagents with conjugated ortho-substituents (phenyl and acetylene groups) were developed to introduce molecular interactions with nanotube sidewalls into the defect-formation chemical reaction. The functionalized chiral SWCNTs selectively emitted single defect PL in the wavelength range of 1230-1270 nm for (6,5) tubes, indicating the formation of an atypical binding configuration, different from those exhibited by typical aryl- or alkyl-functionalized chiral tubes emitting 1150 nm PL. Moreover, the acetylene-based substituent design enabled PL brightening and a subsequent molecular modification of the doped sites using click chemistry.

Original languageEnglish
Pages (from-to)21452-21461
Number of pages10
JournalACS nano
Volume16
Issue number12
DOIs
Publication statusAccepted/In press - 2022

All Science Journal Classification (ASJC) codes

  • General Materials Science
  • General Engineering
  • General Physics and Astronomy

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