Establishing design principles for emissive organic SWIR chromophores from energy gap laws
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Abstract
Rational design of bright near and shortwave infrared (NIR: 700-1000 SWIR: 1000- 2000 nm) emitters remains an open question with applications spanning imaging and photonics. Combining experiment and theory, we derive an energy gap quantum yield master equation (EQME), describing the fundamental limits in SWIR quantum yields (ϕ F ) for organic chromophores. Evaluating the photophysics of 21 polymethine NIR/SWIR chromophores to parameterize the EQME, we explain the precipitous decline of ϕ F past 900 nm through decreasing radiative rates and increasing nonradiative losses via high frequency vibrations relating to the energy gap. Using the EQME we develop an energy gap independent ϕ F NIR/SWIR chromophore comparison metric. We show electron donating character on polymethine heterocycles results in relative increases in radiative efficiency obscured by a simultaneous redshift. Finally, the EQME yields rational chromophore design insights shown by how deuteration (backed by our experimental results) or molecular aggregation increases SWIR ϕ F .
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Significant red-shifts in emission wavelength are primarily achieved through elongation of the polymethine chain and fine structural modifications, including extension or modification of terminal heterocycles, electron-donating or withdrawing substituents on terminal units, and cyclization of the polymethine chain.
“Significant red-shifts in emission wavelength are primarily achieved through two strategies: elongation of the polymethine chain and fine structural modifications, including extension or modification of terminal heterocycles, electron-donating or withdrawing substituents on terminal units and cyclization of the polymethine chain111–113.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [111]
The Introduction and Results section on comparing chromophore quantum yields (page numbers unavailable) report that electron-donating groups on the heterocycle red-shift the flavylium polymethine scaffold. The passages do not establish chain elongation, electron-withdrawing substituents, terminal-heterocycle extension, or polymethine-chain cyclization as red-shifting strategies, nor that the listed strategies are the primary ones. (LLM, conf=0.85)
Experimental — accuracy not yet measuredEach 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 [111]
The Results section on chromophore quantum yield links red-shifting to electron-donating groups, not to inserting methylene units between donor and acceptor. Searches for “methylene,” “100 nm,” and polymethine-chain length found no passage stating the claimed per-unit rule; the available passages have no page numbers. (LLM, conf=0.72)
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“…are primarily achieved through two strategies: elongation of the polymethine chain and fi ne structural modi fi cations, including extension or modi fi cation of terminal hetero-cycles, electron-donating or withdrawing substituents on terminal units and cyclization of the polymethine chain 111 – 113 .”
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- Authors
- Friedman, H. C., Cosco, E. D., Atallah, T. L., Jia, S., Sletten, E. M., & Caram, J. R.
- Affiliations
- University of California, Los Angeles (US)
- Corresponding author
- Caram, Justin R.
- ORCID
- Venue
- Chem
- Publisher
- Elsevier BV
- Published
- 2021-12
- Volume
- 7
- Issue
- 12
- Pages
- 3359-3376
- ISSN
- 2451-9294 (ISSN-L)
- PMC
- PMC8664240
- OpenAlex
- W3154160965
- Cited by
- 145
- References
- 74
- Citations by year
- 2026: 47 · 2025: 19 · 2024: 30 · 2023: 22 · 2022: 17 · 2021: 10
- FWCI
- 5.99
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- www.elsevier.com/tdm/userlicense/1.0/ (tdm)
- www.elsevier.com/legal/tdmrep-license (tdm)
- www.elsevier.com/open-access/userlicense/1.0/ (vor, 373 d)
- doi.org/10.15223/policy-017 (stm-asf)
- doi.org/10.15223/policy-037 (stm-asf)
- doi.org/10.15223/policy-012 (stm-asf)
- doi.org/10.15223/policy-029 (stm-asf)
- doi.org/10.15223/policy-004 (stm-asf)
- Locations
- Chem (publishedVersion)
- ChemRxiv (acceptedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- eScholarship (California Digital Library) (submittedVersion)
- Royal College of Surgeons in Ireland (submittedVersion, cc-by-nc-nd)
- Funders
- NIH (1S10OD016387)
- University of California, Los Angeles (WO2018226720A1, WO2018201000A1, WO2018187295A1)
- National Institute of Biomedical Imaging and Bioengineering (1R01EB027172, CHE-1048804)
- National Science Foundation (DGE-1144087)
- National Science Foundation Division of Chemistry (CHE-1905242, CHE-1945572, CHE-1048804)
- 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 › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Keywords
- near-infrared emitters, organic chromophores, quantum yield, band gap, polymethine dyes, radiative efficiency, non-radiative energy loss, vibrational relaxation, electron-donating substituents, deuteration, molecular aggregation, chromophore design
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