Spontaneously sp2-Carbonized Fluorescent Polyamides as a Probe Material for Bioimaging

Young Jae Jin, Hyojin Kim, Woo Dong Jang, Sang Joon Park, Giseop Kwak

Research output: Contribution to journalArticlepeer-review


Spontaneously sp2-carbonized polyamides (PA1, PA2) were prepared via Knoevenagel-type side reactions of malonyl moieties under mild conditions in the polycondensation of dicarbonyl chloride and diamine. Both polymers were soluble in water and emissive in the visible region, and the fluorescence (FL) intensity and the maximum wavelength were highly dependent on the excitation wavelength and the pH. Their chemical structures and FL origin were clarified by performing various spectroscopic analyses. π*-πtransition was assumed to be allowed in an enol form based on the conjugated structure formed by the side reaction; this was responsible for its pH dependency and high FL quantum efficiency. In particular, PA2, which comprises the tertiary amide linkage, showed quick endocytosis, low cytotoxicity, excellent biocompatibility, and exclusively stained lysosomes with the lowest intracellular pH. These results will help in understanding the origin of the FL emission of carbonized nanomaterials and exploring more advanced functions in the field of bioimaging.

Original languageEnglish
Pages (from-to)3057-3066
Number of pages10
JournalACS Applied Bio Materials
Issue number6
Publication statusPublished - 2022 Jun 20

Bibliographical note

Funding Information:
This work was supported by the Basic Science Research Program of National Research Foundation of Korea (NRF) grants funded by the Korea government (MEST) (2020R1A2C1010980).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Biomaterials
  • Chemistry(all)
  • Biomedical Engineering
  • Biochemistry, medical


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