Shortwave infrared polymethine fluorophores matched to excitation lasers enable non-invasive, multicolour in vivo imaging in real time

Cosco, Emily D.; Spearman, Anthony L.; Ramakrishnan, Shyam; Lingg, Jakob G. P.; Saccomano, Mara; Pengshung, Monica; Arús, Bernardo A.; Wong, Kelly C. Y.; Glasl, Sarah; Ntziachristos, Vasilis; Warmer, Martin; McLaughlin, Ryan; Bruns, Oliver T.; Sletten, Ellen M.

doi:10.1038/s41557-020-00554-5

Cited by 215 publications

(221 citation statements)

References 67 publications

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“…Cosco et al. demonstrated that by using a 7-dimethylamino flavylium heterocycle, the emission of these cyanines can be controllably red-shifted even further, to 1064 nm ( Cosco et al., 2017 , 2020 ). Other work has similarly drawn from the ICG structure to develop polymethine dyes with absorption and emission in the NIR-II region.…”

Section: Organic Dyesmentioning

confidence: 99%

Advances in engineering near-infrared luminescent materials

et al. 2021

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Near-infrared (NIR) luminescent materials have emerged as a growing field of interest, particularly for imaging and optics applications in biology, chemistry, and physics. However, the development of materials for this and other use cases has been hindered by a range of issues that prevents their widespread use beyond benchtop research. This review explores emerging trends in some of the most promising NIR materials and their applications. In particular, we focus on how a more comprehensive understanding of intrinsic NIR material properties might allow researchers to better leverage these traits for innovative and robust applications in biological and physical sciences.

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Section: Organic Dyesmentioning

confidence: 99%

Advances in engineering near-infrared luminescent materials

et al. 2021

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“…IR-26 (2) was purchased from Exciton. Dichloromethane (DCM, HPLC grade) was purchased from Fisher scientific IR-27 (4) and dyes 3-4, 7-15; 1 and 5-6 and 16-21 2 were prepared following reported procedures.…”

Section: Table Of Contentsmentioning

confidence: 99%

“…7-(Dimethylamino)-4-methyl-2phenylchromenylium tetrafluoroborate (S2) was synthesized according to published procedure. 1 5 mmol, 2.5 equiv.) was cooled in ice bath and phospohryl chloride (1.0 mL, 11 mmol, 2.2 equiv.)…”

Section: Overcoming Energy Gap Laws a Enhancement From Changing Maximum Vibrational Stretch Comparing Parametersmentioning

confidence: 99%

“…For dyes 1-16, relative quantum yields were taken with IR-26 as the standard in DCM (detailed methodology in references). 1,2 The Φ of IR-26 (2) was taken to be 5 × 10 −4 in accordance with several recent measurements. [3][4][5] Dyes 17-21 were found using absolute quantum yield with an integrating sphere.…”

mentioning

confidence: 99%

“…The mixture was stirred at 100 °C under N2, cooled and concentrated to dryness. The dark mixture was separated by column chromatography (1:50 EtOH/CH2Cl2) to give 3' as a dark purple solid (17 mg, 0.022 mmol, 27%) 1. H NMR (500 MHz, DMSO) δ 7.99 (s, 6H), 7.61 -7.50 (m, 6H), 7.45 (s, 2H), 6.90 (s, 2H), 6.85 (d, J = 9.0 Hz, 2H), 6.65 (s, 2H), 3.08 (s, 12H), 2.76 (s, 4H), 1.88 (s, 2H).…”

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confidence: 99%

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Establishing Design Principles for Emissive Organic SWIR Chromophores from Energy Gap Laws

Friedman¹,

Cosco²,

Atallah³

et al. 2021

Preprint

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Rational design of bright near and shortwave infrared (NIR: 700–1000 SWIR: 1000–2000 nm) molecular and nanoscale emitters is a fundamental scientific question with applications ranging from deep tissue imaging to new photonic materials. However, all reported organic chromophores with energy gaps in the SWIR have very low quantum yields. Is this the result of a fundamental limit for the quantum yield of organic chromophores in the SWIR? Here we combine experiment and theory to derive an energy gap quantum yield master equation (EQME), which describes the fundamental limits in SWIR quantum yields for organic chromophores in terms of energy gap laws for radiative and nonradiative decay. We parametrize EQME using experimental data from time-correlated single photon counting in the SWIR acquired using superconducting nanowire single photon detectors operating beyond the bandgap of silicon. Evaluating the photophysics of 21 polymethine NIR/SWIR emissive chromophores, we explain the precipitous decline of<sub> </sub> past 900 nm as the result of decreased radiative rates and increased nonradiative deactivation via high frequency vibrations as a function of singlet energy gap. From EQME we can compare quantum yields among NIR/SWIR chromophores while accounting for changes in energy gaps. We find that electron donating character on polymethine heterocycles results in improvements of radiative parameters obscured by a simultaneous redshift. We correlate this improvement to changes in transition dipole moments across the chromenylium polymethine family. Finally, understanding energy gap laws reveals quantitative estimates of the effect of deuteration and molecular aggregation as strategies to increase in the SWIR. We experimentally demonstrate that partial deuteration of the chromophore Flav7 results in decreased nonradiative rates and concomitant increases in quantum yield. These insights will enable optimal chromophore designs for SWIR fluorescence.

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Ultrabright and Highly Polarity‐Sensitive NIR‐I/NIR‐II Fluorophores for the Tracking of Lipid Droplets and Staging of Fatty Liver Disease

Zhou

Zhang

Yang

et al. 2021

Adv Funct Materials

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Visualizing the progression of fatty liver disease in vivo is of great significance in biomedical research of fatty liver, but hindered by the lack of suitable approaches with deep penetration, high specificity, and real-time observability for fatty liver imaging. Herein, two bright NIR-I/NIR-II fluorophores with D-π-A-π-D structures are designed and synthesized for fatty liver tracking in vivo. Such fluorophores show an ultrahigh quantum yield of 49.2% and 17.3% at the emission maximum of 930 and 975 nm, respectively. Most interestingly, these two fluorophores display ultrasensitive fluorescence response (over 100-fold enhancement) toward the variations of environment polarity. Accordingly, further doping of these fluorophores into amphiphilic organic matrix allows the formation of ultrabright NIR-I/NIR-II fluorescent nanoprobes for high-resolution fluorescence imaging of the vessels. Additionally, with the assistance of such nanoprobes and NIR-II fluorescence imaging, real-time monitoring of heartbeat rate and the respiratory rate, accurate identification, and imaging-guided surgery of the submillimeter scale lymph nodes are successfully realized. Moreover, the as-designed fluorophores show superior performance for indicating lipid droplets (LDs) in living cells. Ultimately, precise monitoring of fatty liver with NIR-I/NIR-II fluorescent LDs probe is first confirmed, demonstrating the possibility for staging fatty liver disease with a contact-free method.

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Shortwave infrared polymethine fluorophores matched to excitation lasers enable non-invasive, multicolour in vivo imaging in real time

Cited by 215 publications

References 67 publications

Advances in engineering near-infrared luminescent materials

Advances in engineering near-infrared luminescent materials

Establishing Design Principles for Emissive Organic SWIR Chromophores from Energy Gap Laws

Ultrabright and Highly Polarity‐Sensitive NIR‐I/NIR‐II Fluorophores for the Tracking of Lipid Droplets and Staging of Fatty Liver Disease

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