Amplified fluorescence emission of bolaamphiphilic perylene-azacrown ether derivatives directed towards molecular recognition events

Bappaditya Roy, Takao Noguchi, Daisuke Yoshihara, Tatsuhiro Yamamoto, Junji Sakamoto, Seiji Shinkai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Long-term creative approaches have been considered in the design of molecular probes to overcome the quenching effect of important dyes in an aqueous medium. Using the rational donor-acceptor based design principle, we demonstrate herein the different fluorescence states of a non-conjugated symmetrical perylene-azacrown ether system in a solution, from the molecular to the aggregated states. The ethylene-spacer is exceptionally capable of fluorescence enhancement, even in the aggregated state (organic nanoparticle, ONPs, 44 nm), overcoming the quenching effect on changing the solvent from tetrahydrofuran to water. The ONPs with crown ether receptors at the surface show colloidal stability in an aqueous solution. Furthermore, an improved fluorescent state is developed via ONPs-polymer (protamine, Pro) hybridization. Supramolecular interactions between the crown ring and the guanidinium group in Pro play an important role in the ONPs-Pro hybrid formation. The decorated fluorescent hybrid state is finally used as a nano-probe for sensing heparin via the turn-OFF mechanism. The decoration method is further generalized by recognition of the nucleotides. Herein, we detail the bottom-up approach to the molecular design and development of the different fluorescent states of a useful probe. Most excitingly, this new approach is very general and adaptive to facile detection.

Original languageEnglish
Pages (from-to)13239-13245
Number of pages7
JournalPhysical Chemistry Chemical Physics
Volume18
Issue number19
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Perylene
Molecular recognition
Protamines
Ether
ethers
Fluorescence
Derivatives
fluorescence
probes
Quenching
quenching
heparins
Crown Ethers
Molecular Probes
Guanidine
nucleotides
tetrahydrofuran
spacers
Heparin
Polymers

All Science Journal Classification (ASJC) codes

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Cite this

Amplified fluorescence emission of bolaamphiphilic perylene-azacrown ether derivatives directed towards molecular recognition events. / Roy, Bappaditya; Noguchi, Takao; Yoshihara, Daisuke; Yamamoto, Tatsuhiro; Sakamoto, Junji; Shinkai, Seiji.

In: Physical Chemistry Chemical Physics, Vol. 18, No. 19, 01.01.2016, p. 13239-13245.

Research output: Contribution to journalArticle

Roy, Bappaditya ; Noguchi, Takao ; Yoshihara, Daisuke ; Yamamoto, Tatsuhiro ; Sakamoto, Junji ; Shinkai, Seiji. / Amplified fluorescence emission of bolaamphiphilic perylene-azacrown ether derivatives directed towards molecular recognition events. In: Physical Chemistry Chemical Physics. 2016 ; Vol. 18, No. 19. pp. 13239-13245.
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