Synthesis of Single-Walled Carbon Nanotubes Coated with Thiol-Reactive Gel via Emulsion Polymerization

Yukiko Nagai, Yusuke Tsutsumi, Naotoshi Nakashima, Tsuyohiko Fujigaya

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Single-walled carbon nanotubes (SWNTs) have unique near-infrared absorption and photoemission properties that are attractive for in vivo biological applications such as photothermal cancer treatment and bioimaging. Therefore, a smart functionalization strategy for SWNTs to create biocompatible surfaces and introduce various ligands to target active cancer cells without losing the unique optical properties of the SWNTs is strongly desired. This paper reports the design and synthesis of a SWNT/gel hybrid containing maleimide groups, which react with various thiol compounds through Michael addition reactions. In this hybrid, the method called carbon nanotube micelle polymerization was used to noncovalently modify the surface of SWNTs with a cross-linked polymer gel layer. This method can form an extremely stable gel layer on SWNTs; such stability is essential for in vivo biological applications. The monomer used to form the gel layer contained a maleimide group, which was protected with furan in endo-form. The resulting hybrid was treated in water to induce deprotection via a retro-Diels-Alder reaction and then functionalized with thiol compounds through Michael addition. The functionalization of the hybrid was explored using a thiol-containing fluorescent dye as a model thiol, and the formation of the SWNT-dye conjugate was confirmed by energy transfer from the dye to SWNTs. Our strategy offers a promising SWNT-based platform for biological functionalization for cancer targeting, imaging, and treatment.

Original languageEnglish
Pages (from-to)8544-8550
Number of pages7
JournalJournal of the American Chemical Society
Volume140
Issue number27
DOIs
Publication statusPublished - Jul 11 2018

Fingerprint

Carbon Nanotubes
Emulsion polymerization
Single-walled carbon nanotubes (SWCN)
Emulsions
Sulfhydryl Compounds
Polymerization
Gels
Dyes
Coloring Agents
Addition reactions
Oncology
Neoplasms
Infrared absorption
Photoemission
Micelles
Energy Transfer
Cycloaddition Reaction
Fluorescent Dyes
Energy transfer
Carbon nanotubes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis of Single-Walled Carbon Nanotubes Coated with Thiol-Reactive Gel via Emulsion Polymerization. / Nagai, Yukiko; Tsutsumi, Yusuke; Nakashima, Naotoshi; Fujigaya, Tsuyohiko.

In: Journal of the American Chemical Society, Vol. 140, No. 27, 11.07.2018, p. 8544-8550.

Research output: Contribution to journalArticle

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