Incorporation of Planar Blocks into Twisted Skeletons: Boosting Brightness of Fluorophores for Bioimaging beyond 1500 Nanometer
Abstract
The brightness of organic fluorescence materials determines their resolution and sensitivity in fluorescence display and detection. However, strategies to effectively enhance the brightness are still scarce. Conventional planar π-conjugated molecules display excellent photophysical properties as isolated species but suffer from aggregation-caused quenching effect when aggregated owing to the cofacial π–π interactions. In contrast, twisted molecules show high photoluminescence quantum yield (ΦPL) in aggregate while at the cost of absorption due to the breakage in conjugation. Therefore, it is challenging to integrate the strong absorption and high solid-state ΦPL, which are two main indicators of brightness, into one molecule. Herein, we propose a molecular design strategy to boost the brightness through the incorporation of planar blocks into twisted skeletons. As a proof-of-concept, twisted small-molecule TT3-oCB with larger π-conjugated dithieno[3,2-b:2′,3′-d]thiophene unit displays superb brightness at the NIR-IIb (1500–1700 nm) than that of TT1-oCB and TT2-oCB with smaller thiophene and thienothiophene unit, respectively. Whole-body angiography using TT3-oCB nanoparticles presents an apparent vessel width of 0.29 mm. Improved NIR-IIb image resolution is achieved for femoral vessels with an apparent width of only 0.04 mm. High-magnification through-skull microscopic NIR-IIb imaging of cerebral vasculature gives an apparent width of ∼3.3 μm. Moreover, the deeply located internal organ such as bladder is identified with high clarity. The present molecular design philosophy embodies a platform for further development of in vivo bioimaging.
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The π-spacer plays an important role in tuning the energy levels of D-π-A-π-D chromophores by extending π-conjugation that promotes/stabilizes the quinoid structure or by introducing steric effects to control the overall twist affecting ICT properties.
“As stated above, the π-spacer also plays an important role in tuning the energy levels of the D-π-A-π-D type of chromophores, as it extends the π-conjugation that promotes/stabilizes the quinoid structure or introduces steric effects to control the overall twist affecting the ICT properties of the system.56,58−61”
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”
A recent study reported that a synergetic effect of conformational rigidification that leads to AIE and suppression of access to the TICT state greatly enhances fluorescence brightness of small-molecule fluorophores in an aggregate state.
“A recent study reported that a synergetic effect of conformational rigidification that leads to AIE and suppression of access to the TICT state greatly enhances fluorescence brightness of small-molecule fluorophores in an aggregate state.”
A D-A-D-type molecule, TT3-oCB, consisting of a benzobisthiadiazole (BBTD) acceptor and triphenylamine (TPA) donor that also acts as molecular rotor displayed dim fluorescence in a solution, whereas they exhibited fivefold brighter fluorescence in the aggregate state.
“A D-A-D-type molecule, TT3-oCB, consisting of a benzobisthiadiazole (BBTD) acceptor and triphenylamine (TPA) donor that also acts as molecular rotor displayed dim fluorescence in a solution, whereas they exhibited fivefold brighter fluorescence in the aggregate state (Figure 7b).61”
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- Authors
- Liu, S., Chen, R., Zhang, J., Li, Y., He, M., Fan, X., Zhang, H., Lu, X., Kwok, R. T. K., Lin, H., Lam, J. W. Y., Qian, J., & Tang, B. Z.
- Affiliations
- Hong Kong University of Science and Technology (HK)
- State Key Laboratory of Modern Optical Instruments (CN)
- Sir Run Run Shaw Hospital (CN)
- Corresponding author
- Qian, Jun
- Tang, Ben Zhong
- ORCID
- Venue
- ACS Nano
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-10-01
- Volume
- 14
- Issue
- 10
- Pages
- 14228-14239
- ISSN
- 1936-0851 (ISSN-L)
- 1936-086X
- OpenAlex
- W3089655029
- Cited by
- 129
- References
- 58
- Citations by year
- 2026: 10 · 2025: 25 · 2024: 23 · 2023: 21 · 2022: 25 · 2021: 24 · 2020: 1
- FWCI
- 6.91
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- ACS Nano (publishedVersion)
- PubMed (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- Research Grants Council, University Grants Committee (AHKUST605/16, C6009-17G)
- Innovation and Technology Commission (ITCCNERC14SC01, ITCPD/17-9)
- National Natural Science Foundation of China (21788102, 21805002, 61735016, 61975172)
- Natural Science Foundation of Zhejiang Province (LR17F050001)
- Shenzhen Municipality (JCYJ20180507183832744)
- Ming Wai Lau Centre for Reparative, Karolinska Institutet
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Keywords
- twisted molecules, aggregation-caused quenching, photoluminescence quantum yield, dithienothiophene, small-molecule fluorophores, cerebrovascular imaging, bladder imaging, bioimaging
- MeSH terms
- Fluorescence, Fluorescent Dyes, Skeleton, Thiophenes, Nanoparticles
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