Thienothiadiazole-Based NIR-II Dyes with D–A–D Structure for NIR-II Fluorescence Imaging Systems
Abstract
Fluorescence imaging (FI) in the second near-infrared optical window (NIR-II, 1000–1700 nm) has received increasing focus due to its capacity of high spatiotemporal resolution, rapid real-time imaging, and deep penetration depth. In addition, D–A–D-based organic small molecules have also attracted wide attention due to their designed chemical structure and rapid renal metabolism. However, most of the fluorescent cores were based on benzobisthiadiazole (BBTD) and 6,7-diphenyl-[1,2,5]thiadiazolo[3,4- g ]quinoxaline (TTQ). The design and development of fluorescent core still remain challenging. Therefore, two NIR-II dyes based on the acceptor 4,6-di(2-thienyl)thieno[3,4- c ][1,2,5]thiadiazole (TTDT) were designed and developed with donors tributyl(5-(9,9-dioctyl-9H-fluoren-2-yl)thiophen-2-yl)stannane (TF) and (5-(9,9′-spirobi[fluoren]-2-yl)thiophen-2-yl)tributylstannane (TSF) by the Stille coupling reaction, respectively. Subsequently, the corresponding nanoparticles were prepared, and then TTDT-TF-based nanoparticles with superior photostability and strong NIR-II fluorescence signals were chosen for NIR-II FI. More importantly, the in vivo experiments suggested that TTDT-TF NPs exhibited significant accumulation at tumor sites and high signal-to-background ratio (SBR). The above results indicated that the two D–A–D-type fluorophores based on TTDT have potential for NIR-II FI with superior imaging quality and imaging-guided surgery or therapy.
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On the basis of a consecutive incorporation of common rotors (triphenylamine (TPA), TPE) as electron-donating groups that are directly conjugated to the acceptor unit or introduced to the donor groups, a number of new D-A-D dyes have been developed.
“On the basis of a consecutive incorporation of common rotors (triphenylamine (TPA), TPE) as electron-donating groups that are directly conjugated to the acceptor unit or introduced to the donor groups, a number of new D-A-D dyes have been developed.52,61,145−148”
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 [146]
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- Authors
- Sun, P., Chen, Y., Sun, B., Zhang, H., Chen, K., Miao, H., Fan, Q., & Huang, W.
- Affiliations
- Nanjing University of Posts and Telecommunications (CN)
- Northwestern Polytechnical University (CN)
- Corresponding author
- Sun, Pengfei
- Miao, Han
- Fan, Quli
- Venue
- ACS Applied Bio Materials
- Publisher
- American Chemical Society (ACS)
- Published
- 2021-04-29
- Volume
- 4
- Issue
- 5
- Pages
- 4542-4548
- ISSN
- 2576-6422 (ISSN-L)
- OpenAlex
- W3157680146
- Cited by
- 27
- References
- 35
- Citations by year
- 2026: 3 · 2025: 7 · 2024: 4 · 2023: 7 · 2022: 6
- FWCI
- 1.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- ACS Applied Bio Materials (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Natural Science Foundation of Jiangsu Province (BK20201380)
- Synergetic Innovation Center for Organic Electronics and Information Displays
- National Natural Science Foundation of China (21604042, 21674048)
- Primary Research & Development Plan of Jaingsu Province (BE2016770)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
- Keywords
- NIR-II fluorescence imaging, Stille coupling, fluorescent nanoparticles, tumor accumulation, photostability, image-guided surgery
- MeSH terms
- Density Functional Theory, Animals, Biocompatible Materials, Fluorescent Dyes, Infrared Rays, Materials Testing, Particle Size, Thiadiazoles, Thiophenes, Molecular Structure, Rats, Optical Imaging
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