Acid/base and H2PO4- controllable high-contrast optical molecular switches with a novel BODIPY functionalized [2]rotaxane

Reguram Arumugaperumal, Venkatesan Srinivasadesikan, Mandapati V. Ramakrishnam Raju, Ming Chang Lin, Tarun Shukla, Ravinder Singh, Hong Cheu Lin

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

A novel multifunctional mechanically interlocked switchable [2]rotaxane R4 containing two molecular stations and rotaxane arms terminated with boron-dipyrromethene (BODIPY) fluorophores and its derivatives were synthesized for the first time by CuAAC click reaction. The shuttling motion of macrocycle between the dibenzylammonium and triazolium recognition sites and the distance dependent photoinduced electron transfer process of R4 is demonstrated by utilizing external chemical stimuli (acid/base). Interestingly, the reversible self-assembly process of R4 was recognized by the acid-base molecular switch strategy. Notably, two symmetrical triazolium groups acted as molecular stations, H2PO4- receptors, and H-bonded donors. Both [2]rotaxane R4 and thread R2 demonstrated excellent optical responses and high selectivity toward H2PO4- ion. The specific motion and guest-host interactions of mechanically interlocked machines (MIMs) were also further explored by quantum mechanical calculations. The thread R2 also demonstrated to enable the detection of H2PO4- in RAW 264.7 cells successfully.

Original languageEnglish (US)
Pages (from-to)26491-26503
Number of pages13
JournalACS Applied Materials and Interfaces
Volume7
Issue number48
DOIs
StatePublished - Dec 9 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

Keywords

  • BODIPY
  • ESP
  • HPO ion sensor
  • PM3 level
  • and bioimaging
  • molecular motion
  • switchable [2]rotaxane

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