Manipulating electron transfer between single-walled carbon nanotubes and diazonium salts for high purity separation by electronic type

Young Jin Do, Jong Hwa Lee, Hyerim Choi, Jae Hee Han, Chan Hwa Chung, Myung Gi Jeong, Michael S. Strano, Woo Jae Kim

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Diazonium salts preferentially react with metallic single-walled carbon nanotubes (SWNT) over semiconducting SWNT, enabling the separation of SWNT by electronic type. Therefore, the reaction selectivity of diazonium salts for metallic SWNT is crucial for high purity separation of both metallic and semiconducting SWNT. Herein, we developed an efficient method of increasing the reaction selectivity by manipulating the redox potential of diazonium salts. The electron affinity of diazonium salts is effectively lowered when the para-substituent of the diazonium salts is an electron-donating group, (i.e., 4-hydroxy and 4-propargyloxy) rather than an electron-withdrawing group (i.e., 4-nitro, 4-carboxy, and 4-cholro). The reduction potential of 4-hydroxyphenyl and 4-propargyloxyphenyl diazonium salt was greater than the oxidation potential of semiconducting SWNT; therefore, the electron transfer reaction between these two reagents was effectively suppressed, leading to a highly selective reaction for metallic SWNT. We confirmed that this highly selective reaction scheme can be used to separate SWNT, and high purity semiconducting SWNT can be obtained via density-induced separation.

Original languageEnglish
Pages (from-to)4146-4151
Number of pages6
JournalChemistry of Materials
Volume24
Issue number21
DOIs
StatePublished - 13 Nov 2012

Keywords

  • diazonium
  • redox potential
  • selective functionalization
  • single-walled carbon nanotubes

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