Shortwave infrared-absorbing squaraine dyes for all-organic optical upconversion devices
Open accessAbstract
Shortwave infrared (SWIR) optical sensing and imaging are essential to an increasing number of next-generation applications in communications, process control or medical imaging. An all-organic SWIR upconversion device (OUC) consists of an organic SWIR sensitive photodetector (PD) and an organic light-emitting diode (OLED), connected in series. OUCs directly convert SWIR to visible photons, which potentially provides a low-cost alternative to the current inorganic compound-based SWIR imaging technology. For OUC applications, only few organic materials have been reported with peak absorption past 1000 nm and simultaneous small absorption in the visible. Here, we synthesized a series of thermally stable high-extinction coefficient donor-substituted benz[cd]indole-capped SWIR squaraine dyes. First, we coupled the phenyl-, carbazole-, and thienyl-substituted benz[cd]indoles with squaric acid (to obtain the SQ dye family). We then combined these donors with the dicyanomethylene-substituted squaraine acceptor unit, to obtain the dicyanomethylene-functionalized squaraine DCSQ family. In the solid state, the absorbance of all dyes extended considerably beyond 1100 nm. For the carbazole- and thienyl-substituted DCSQ dyes, even the peak absorptions in solution were in the SWIR, at 1008 nm and 1014 nm. We fabricated DCSQ PDs with an external photon-to-current efficiency over 30%. We then combined the PD with a fluorescent OLED and fabricated long-term stable OUCs with peak sensitivity at 1020 nm, extending to beyond 1200 nm. Our OUCs are characterized by a very low dark luminance (<10−2 cd m−2 at below 6 V) in the absence of SWIR light, and a low turn-on voltage of 2 V when SWIR light is present.
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A family of benz[cd]indole-capped SWIR squaraine dyes has been synthesized by coupling phenyl-, carbazole-, and thienyl-substituted benz[cd]indoles with squaric acid.
“In addition, a family of benz[cd]indole-capped SWIR squaraine dyes has been synthesized by coupling phenyl- (e.g., DCSQ2), carbazole- (e.g., DCSQ3), and thienyl- (e.g., DCSQ4) substituted benz [cd]indoles with squaric acid.68”
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 [68]
The Synthesis section confirms that phenyl-, carbazole-, and thiophene-substituted benz[cd]indole donors were used to make both SQ and DCSQ dye families. But it distinguishes their routes: the SQ dyes were made by condensation with squaric acid, whereas the cited DCSQ examples were made with dicyano squarate 11. The claim conflates the two routes. (LLM, conf=0.90)
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Sreejith, S., Sanjay, C., Vedhanarayanan, B., & Ajayaghosh, A. (2026) · Chemical Society Reviews · doi:10.1039/d5cs01375e · Cited by 5 · see citing works
Squaraine dye: Promising strategies to boost power conversion efficiencies of OPV cells
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Near-infrared up-conversion organic light-emitting devices
Shi, Y., & Hu, Y. H. (2024) · Optoelectronic devices and integration. Conference · doi:10.1117/12.3035672
“[4-6] This method enables the generation of high-quality, pixel-free infrared images without the necessity for high-density readout integrated circuits, thereby reducing costs.”
Shi, L., Shi, Z., CHANG, M., Gao, Z., Cui, Y., Ji, T., & Li, G. (2026) · Laser & Photonics Review · doi:10.1002/lpor.202501543
“…nm, 8 V 0.96 ∼ 1.0 × 10 10 2020 [ 40 ] DPP-DTT:SWIR dye ∼ 14@1200 nm, − 2 V ∼ 0.14 — 2021 [ 41 ] SQ-H:PC 61 BM 24.1@1050 nm, − 2 V 0.20 — 2021 [ 42 ] DCSQ1:PCBM 33@1025 nm, − 8 V 0.27 — 2021 [ 43 ] PolyTPD:BCF ∼ 44.47@1500 nm, − 30 V ∼ 0.54 — 2022 [ 30 ] CDT-TQ:PC 70 BM:CA 5.60 × 10 2 @1050…”
InfluentialHan, X., He, M., Zhao, F., Wei, S., Xiang, M., Liu, Y., Qiang, X., Yao, M., Xie, Z., Guo, L., et al. (2026) · Laser & Photonics Review · doi:10.1002/lpor.71853
Giavazzi, D., Assunção, J. P. F., Bauer, M., Diethelm, M., Hu, W., Jafarpour, M., Widmer, R., Neels, A., Sapalidis, D., Silva, B. F. B., et al. (2026) · Advanced Functional Materials · doi:10.1002/adfm.78546
Self-citationDidier, E., Bannwart, J., Bauer, M., Assunção, J. P. F., Rentsch, D., Nüesch, F. A., & Hany, R. (2026) · Small · doi:10.1002/smll.76112
Self-citationBauer, M., Didier, E., Assunção, J. P. F., Richeboeuf, L., Nüesch, F. A., Rentsch, D., Padula, D., & Hany, R. (2026) · Science and Technology of Advanced Materials · doi:10.1080/14686996.2026.2732506
Self-citation
- Authors
- Strassel, K., Hu, W.-H., Osbild, S., Padula, D., Rentsch, D., Yakunin, S., Shynkarenko, Y., Kovalenko, M., Nüesch, F., Hany, R., & Bauer, M.
- Affiliations
- École Polytechnique Fédérale de Lausanne (CH)
- Empa (CH)
- University of Siena (IT)
- Laboratory of Inorganic Chemistry (CH)
- Corresponding author
- Hany, Roland
- ORCID
- Venue
- Science and Technology of Advanced Materials
- Publisher
- Informa UK Limited
- Published
- 2021-04-13
- Volume
- 22
- Issue
- 1
- Pages
- 194-204
- ISSN
- 1468-6996 (ISSN-L)
- 1878-5514
- PMC
- PMC8049466
- OpenAlex
- W3135397317
- Cited by
- 27
- References
- 61
- Citations by year
- 2026: 6 · 2025: 4 · 2024: 3 · 2023: 6 · 2022: 4 · 2021: 4
- FWCI
- 1.25
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Science and Technology of Advanced Materials (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DORA Empa (Swiss Federal Laboratories for Materials Science and Technology (Empa)) (submittedVersion, cc-by)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Infoscience (Ecole Polytechnique Fédérale de Lausanne) (submittedVersion, cc-by-nc-nd)
- Use Siena air (University of Siena) (submittedVersion, other-oa)
- Repository for Publications and Research Data (ETH Zurich) (submittedVersion, cc-by)
- ETH Zürich Research Collection (cc-by)
- Funders
- Italian Ministry of Education, University, and Research (Rita Levi Montalcini grant)
- Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (206021_150638/1, IZBRZ2_186261, IZRJZ2_164179)
- Topics
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Electronics and Photovoltaics
- Keywords
- squaraine dyes, organic photodetectors, organic light-emitting diodes, donor-acceptor dyes, SWIR imaging, turn-on voltage, thermal stability
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