Design, Synthesis, and Application of a Small Molecular NIR-II Fluorophore with Maximal Emission beyond 1200 nm

Fang, Yu; Shang, Jizhen; Liu, Diankai; Shi, Wen; Li, Xiaohua; Ma, Huimin

doi:10.1021/jacs.0c08187

Cited by 223Luminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionOptical Imaging and Spectroscopy Techniques

Design, Synthesis, and Application of a Small Molecular NIR-II Fluorophore with Maximal Emission beyond 1200 nm

Fang, Yu, Shang, Jizhen, Liu, Diankai, Shi, Wen, Li, Xiaohua, Ma, Huimin·2020·Journal of the American Chemical Society

DOI 10.1021/jacs.0c08187

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Abstract

Small molecular fluorophores in the second near-infrared window (NIR-II) have aroused much interest because of their excellent performance. Herein, a new small molecular NIR-II fluorophore, FM1210, with maximal emission beyond 1200 nm is reported. Compared to the corresponding control fluorophore CF1065, FM1210 exhibits an increase of 145 nm in the emission maximum, which is ascribed to the simultaneous introduction of both a Se atom and amino groups into the benzo[1,2- c:4,5- c ′]bis([1,2,5]thiadiazole) skeleton. This large increase in the maximal emission enables FM1210 to be capable of in vivo imaging with lower autofluorescence, higher signal-to-background ratio, and better resolution. Moreover, nanosized FM1210 encapsulated in liposomes possesses passive targeting ability and good water solubility, and is suitable for imaging a tumor and even its vasculature with high signal-to-background ratio.

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Each methylene unit inserted between donor and acceptor typically induces a red-shift of ~100 nm.
“A general rule, as exemplified in cyanine dyes, is that each methylene unit inserted between donor and acceptor typically induces a red-shift of ~100 nm111–123.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [115]
Replacing the S atom with Se in the BBT skeleton shifts fluorescence emission far beyond 1200 nm (e.g., FM1210).
“By replacing the S atom with Se in the BBT skeleton, fluorescence emission can be shifted far beyond 1200 nm (e.g., FM1210).48”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [48]
The BBTD core and its derivatives are potent electron-accepting units with excellent quantum efficiency, making them ideal for low-bandgap polymers and long-wavelength NIR-II fluorophores.
“The benzobisthiadiazole (BBTD) core and its derivatives are potent electron-accepting units with excellent quantum efficiency, making them ideal for the design of low-bandgap polymers and long-wavelength NIR-II fluorophores (Fig. 5 and Table 2)114–150.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [115]

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Authors: Fang, Y., Shang, J., Liu, D., Shi, W., Li, X., & Ma, H.
Affiliations: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Chinese Academy of Sciences (CN)
Corresponding author: Shi, Wen
Ma, Huimin
ORCID: Liu, Diankai
Shi, Wen
Li, Xiaohua
Ma, Huimin
Venue: Journal of the American Chemical Society
Publisher: American Chemical Society (ACS)
Published: 2020-08-21
Volume: 142
Issue: 36
Pages: 15271-15275
ISSN: 0002-7863 (ISSN-L)
1520-5126
DOI: 10.1021/jacs.0c08187
OpenAlex: W3080620088
Cited by: 223
References: 34
Citations by year: 2026: 21 · 2025: 38 · 2024: 42 · 2023: 37 · 2022: 46 · 2021: 37 · 2020: 2
FWCI: 11.87
Type: journal article
Language: en
Open access: closed
Licence: doi.org/10.15223/policy-029 (stm-asf)
doi.org/10.15223/policy-037 (stm-asf)
doi.org/10.15223/policy-045 (stm-asf)
Locations: Journal of the American Chemical Society (publishedVersion)
PubMed (publishedVersion)
Funders: Youth Innovation Promotion Association of the Chinese Academy of Sciences (2016027)
National Natural Science Foundation of China (21535009, 21675159, 21775152, 21820102007, 21922412)
Topics: Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Optical Imaging and Spectroscopy Techniques
Keywords: in vivo imaging, tumor imaging, tumor vasculature imaging, passive targeting, autofluorescence suppression

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Design, Synthesis, and Application of a Small Molecular NIR-II Fluorophore with Maximal Emission beyond 1200 nm

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