Synthesis of near-infrared fluorescent two-photon-absorbing fluorenyl benzothiadiazole and benzoselenadiazole derivatives

Sheng Yao, Bosung Kim, Xiling Yue, Maria Y. Colon Gomez, Mykhailo V. Bondar, Kevin D. Belfield

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A series of dyes 2−5 based on 5-thienyl-2,1,3-benzothiadiazole and 5-thienyl-2,1,3-benzoselenadiazole cores were synthesized as near-infrared-emitting two-photon-absorbing fluorophores. Fluorescence maxima wavelengths as long as 714 nm and quantum yields as high as 0.67 were realized. The fluorescence quantum yields of dyes 2−4 were nearly constant, regardless of solvent polarity. These diazoles exhibited large Stokes shifts (>110 nm) and high two-photon figure of merit. Cells incubated on a 3D scaffold with probe 4 (encapsulated in Pluronic micelles) exhibited bright fluorescence, enabling 3D two-photon fluorescence imaging to a depth of 100 μm.

Original languageEnglish (US)
Pages (from-to)1149-1156
Number of pages8
JournalACS Omega
Volume1
Issue number6
DOIs
StatePublished - 2021

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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