Large red-shifted NIR absorption in azulenyl- and iodinated-modified BODIPYs sensitive to aggregation and protonation stimuli

Zhao, Chunrui; Wu, Bin; Yang, Jufang; Baryshnikov, Glib; Zhou, Yunyun; Ågren, Hans; Zou, Qi; Zhu, Liangliang

doi:10.1016/j.dyepig.2021.109867

Cited by 6 publications

(5 citation statements)

References 44 publications

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“…Interestingly, the proton was added at the 5-position (at a carbon) of the indolizine. This protonated structure ( Figure 4 a) was consistent with other examples in the literature of SWIR-emitting BODIPY dyes where an additional cation has been introduced in conjugation via synthetic design or protonation [ 46 , 48 ]. 1Ph-TFA exhibited a 954 nm vertical transition ( Table S1 from Supplementary Materials ), which was 0.33 eV lower in energy than that of neutral 1Ph .…”

Section: Resultssupporting

confidence: 87%

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Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes

et al. 2023

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Fluorescent organic dyes that absorb and emit in the near-infrared (NIR, 700–1000 nm) and shortwave infrared (SWIR, 1000–1700 nm) regions have the potential to produce noninvasive high-contrast biological images and videos. BODIPY dyes are well known for their high quantum yields in the visible energy region. To tune these chromophores to the NIR region, fused nitrogen-based heterocyclic indolizine donors were added to a BODIPY scaffold. The indolizine BODIPY dyes were synthesized via microwave-assisted Knoevenagel condensation with indolizine aldehydes. The non-protonated dyes showed NIR absorption and emission at longer wavelengths than an aniline benchmark. Protonation of the dyes produced a dramatic 0.35 eV bathochromic shift (230 nm shift from 797 nm to 1027 nm) to give a SWIR absorption and emission (λmaxemis = 1061 nm). Deprotonation demonstrates that material emission is reversibly switchable between the NIR and SWIR.

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Section: Resultssupporting

confidence: 87%

“…Inspired by the dramatic bathochromic shift in absorption and emission upon the treatment of azulene BODIPY dyes with trifluoroacetic acid (TFA) that was reported by Zhao, et al [ 46 ], DMA , 2Ph , and 1Ph were subjected to 1% TFA solution in CH 2 Cl 2 (ca. 10 μM dye concentration, Figure 3 b).…”

Section: Resultsmentioning

confidence: 99%

Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes

et al. 2023

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“…Thus, the pyrene triplet state is involved in upconversion. In the absence of the sensitizer, upconversion absorption at a wavelength of 540 nm can be ascertained as pyrene aggregation, which may absorb light at longer wavelengths. , Furthermore, the upconverted excitation spectrum of pyrene in ACN is somewhat different from the absorption spectrum of pyrene in TZP, which indicates that multiple absorption moieties are present. Owing to the water in wet solvents and resulting pyrene aggregation, upconverted spectra were also observed for pyrene in solvents, such as water (H 2 O), dimethyl sulfoxide (DMSO), N , N -dimethylformamide (DMF), dichloromethane (DCM), chloroform, and tetrahydrofuran [THF) (Figure S4 (left)].…”

Section: Resultsmentioning

confidence: 99%

Aggregation-Induced Fluorescence Upconversion of Pyrene under Low Fluence: In Solutions and Polymeric Nanoparticles

Banerjee,

De,

Bhattacharjee

2024

J. Phys. Chem. B

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In this study, aggregation-induced photon upconversion (iPUC) is demonstrated in the small polyaromatic molecule, pyrene. In binary-solvent mixtures, water, which induces the aggregation of polyaromatic molecules, assisted in triplet–triplet annihilation-based upconversion. No upconverted emission was observed in a dry solvent. Although upconverted emission in the absence of a triplet sensitizer was assigned to pyrene-aggregate-induced sensitization, the presence of a triplet sensitizer enhanced the upconversion efficiency. This experimental finding was further simulated to explore the possibility of iPUC in the condensed-phase polymer matrix. We studied 2-aminoethyl methacrylate hydrochloride–polystyrene copolymer nanoparticles embedded with the molecular upconversion system. The nanoparticle iPUC agreed with the proposition that water domains were present in polymer nanoparticles and helped aggregate pyrene in the host polymer. Despite the low systemic upconversion efficiency, this study provides a method for achieving fluorescence upconversion in relatively simple systems.

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“…The presence of electron donor groups conjugated with the π-system in the molecule was found to increase Φ ∆ [149]. Expansion of the π-system from phenyl to polyaromatic substituents does not result in either a shift to the IR region or an increase in ROS generation, but presumably increases toxicity in the dark [150][151][152][153][154]. Glytamic acid-derived aza-BODIPY 96 has good water solubility and high ROS generation.…”

Section: O2 Generatorsmentioning

confidence: 96%

Near-Infrared Dyes: Towards Broad-Spectrum Antivirals

Mariewskaya

Krasilnikov

Korshun

et al. 2022

IJMS

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Broad antiviral activity in vitro is known for many organic photosensitizers generating reactive oxygen species under irradiation with visible light. Low tissue penetration of visible light prevents further development of antiviral therapeutics based on these compounds. One possible solution to this problem is the development of photosensitizers with near-infrared absorption (NIR dyes). These compounds found diverse applications in the photodynamic therapy of tumors and bacterial infections, but they are scarcely mentioned as antivirals. In this account, we aimed to evaluate the therapeutic prospects of various NIR-absorbing and singlet oxygen-generating chromophores for the development of broad-spectrum photosensitizing antivirals.

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Large red-shifted NIR absorption in azulenyl- and iodinated-modified BODIPYs sensitive to aggregation and protonation stimuli

Cited by 6 publications

References 44 publications

Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes

Acid-Triggered Switchable Near-Infrared/Shortwave Infrared Absorption and Emission of Indolizine-BODIPY Dyes

Aggregation-Induced Fluorescence Upconversion of Pyrene under Low Fluence: In Solutions and Polymeric Nanoparticles

Near-Infrared Dyes: Towards Broad-Spectrum Antivirals

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