Photo-conversion of self-assembled structures into continuous covalent structures via [2 + 2]-cycloaddition reactions

Moeka Inada, Akihiro Udagawa, Sota Sato, Toru Asahi*, Kei Saito

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, the conversion of self-assembled structures into continuous polymeric structures by linking the self-assembled molecules using the [2 + 2]-cycloaddition reaction was investigated. Synthesized bio-inspired thymine-based bolaamphiphilic molecules were designed to force the interactions between two molecules to engage two thymines in their self-assembled structure to undergo a cycloaddition reaction. Thymine-based bolaamphiphilic molecules were designed and synthesized using different phenylene spacers based on aromatic substituents (ortho-) (meta-) (para-). The formed self-assembled structures from these molecules were characterized and compared using molecular mechanical simulations. Simulations were performed to discuss the relationship between the inter- and intramolecular cycloaddition sensitivity to different substituents. This study provides a strategy for creating higher molecular weight linear polymers by controlling the photocyclization sites within the self-assembly by spacers between thymines. Graphical abstract: An intermolecular [2 + 2] cycloaddition reaction of thymine-based bolaamphiphilic molecules proceeded within the self-assembled nano-ribbon-like structure to form the continuous covalent structure. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)2169-2177
Number of pages9
JournalPhotochemical and Photobiological Sciences
Volume21
Issue number12
DOIs
Publication statusPublished - 2022 Dec

Keywords

  • Dynamic covalent bonding
  • Self-assembly
  • Thymine
  • [2 + 2] cycloaddition

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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