Photophysical Tuning of Shortwave Infrared Flavylium Heptamethine Dyes via Substituent Placement
Open accessAbstract
Optical imaging in the shortwave infrared region (SWIR, 1000–2000 nm) provides high-resolution images in complex systems. Here we explore substituent placement on dimethylamino flavylium polymethine dyes, a class of SWIR fluorophores. We find that the position of the substituent significantly affects the λ max and fluorescence quantum yield. Quantum-mechanical calculations suggest that steric clashes control the extent of π-conjugation. These insights provide design principles for the development of fluorophores for enhanced SWIR imaging.
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Progressive spectral red-shifts have been achieved by introducing the dimethylamino group at different positions of the flavylium heterocycle.
“Progressive spectral red-shifts have further been achieved by the introduction of the dimethylamino group at different positions of the flavylium heterocycle.39”
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 [39]
The Results and Discussion report a 20 nm red-shift when the dimethylamino group is moved from the seven- to the six-position. But the five- and eight-position dyes are blue-shifted relative to the seven-position dye, contrary to a progressive series of red-shifts. (LLM, conf=0.88)
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- Authors
- Pengshung, M., Li, J., Mukadum, F., Lopez, S. A., & Sletten, E. M.
- Affiliations
- University of California, Los Angeles (US)
- Northeastern University (US)
- Corresponding author
- Lopez, Steven A.
- Sletten, Ellen M.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2020-07-29
- Volume
- 22
- Issue
- 15
- Pages
- 6150-6154
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- PMC
- PMC7542986
- OpenAlex
- W3046170579
- Cited by
- 42
- References
- 34
- Citations by year
- 2026: 9 · 2025: 3 · 2024: 5 · 2023: 4 · 2022: 10 · 2021: 10 · 2020: 1
- FWCI
- 2.43
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Licence
- Locations
- Organic Letters (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Alfred P. Sloan Foundation (FG-2018-10855)
- National Institute of Biomedical Imaging and Bioengineering (1R01EB027172)
- Division of Advanced Cyberinfrastructure (1940307)
- National Science Foundation (CHE-1905242)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Keywords
- fluorescence quantum yield, steric effects, π-conjugation, quantum chemical calculations
- MeSH terms
- Fluorescent Dyes, Infrared Rays, Molecular Structure, Optical Imaging
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