A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton: Synthesis, photophysical property, and bio-imaging applications for cells and tissues

Yuna Jung, Youngseo Kim, Na Hee Kim, Junho Lee, Kang Hoon Kim, Junyang Jung, Youngbuhm Huh, Hyeung Jin Jang, Jinmyoung Joo, Sungnam Park, Dokyoung Kim

Research output: Contribution to journalArticle

Abstract

A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)2), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.

LanguageEnglish
Pages104-111
Number of pages8
JournalDyes and Pigments
Volume162
DOIs
Publication statusPublished - 2019 Mar 1

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Naphthalene
Microscopic examination
Tissue
Imaging techniques
Wavelength
Nitriles
Electrons
Cell membranes
Aldehydes
Fluorescent Dyes
Hydroxyl Radical
Demonstrations
Carbon
Photons
Fluorescence
Membranes
Scanning
Lasers
naphthalene

Keywords

  • Bio-imaging
  • Fluorescence imaging
  • Fluorophore
  • Membrane probe
  • Two-photon imaging

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton : Synthesis, photophysical property, and bio-imaging applications for cells and tissues. / Jung, Yuna; Kim, Youngseo; Kim, Na Hee; Lee, Junho; Kim, Kang Hoon; Jung, Junyang; Huh, Youngbuhm; Jang, Hyeung Jin; Joo, Jinmyoung; Park, Sungnam; Kim, Dokyoung.

In: Dyes and Pigments, Vol. 162, 01.03.2019, p. 104-111.

Research output: Contribution to journalArticle

Jung, Yuna ; Kim, Youngseo ; Kim, Na Hee ; Lee, Junho ; Kim, Kang Hoon ; Jung, Junyang ; Huh, Youngbuhm ; Jang, Hyeung Jin ; Joo, Jinmyoung ; Park, Sungnam ; Kim, Dokyoung. / A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton : Synthesis, photophysical property, and bio-imaging applications for cells and tissues. In: Dyes and Pigments. 2019 ; Vol. 162. pp. 104-111.
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abstract = "A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)2), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.",
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