Red-to-NIR emissive radical cations derived from simple pyrroles

Zheng, Lihua; Zhu, Wenchao; Zhou, Zikai; Li, Kai; Gao, Meng; Tang, Ben Zhong

doi:10.1039/d1mh01121a

Cited by 28 publications

(17 citation statements)

References 47 publications

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“…They have been widely investigated and found to have versatile applications in the fields of organic synthesis, 1–4 photoelectronic devices, 5,6 and biotechnology. 7–9 Extensive attempts have been made to investigate the photophysical properties of these sensitive radicals. For example, there are many examples for nitrogen-containing photochromic systems, such as hexaarylbiimidazole derivatives, 10 2,4,6-tri(4-pyridyl)-1,3,5-triazine, 11 phenothiazine-poly(dimethylsiloxane) hybrids, 12 tri- p -tolylamine, 13–15 etc.…”

Section: Introductionmentioning

confidence: 99%

Manipulating D–A interaction to achieve stable photoinduced organic radicals in triphenylphosphine crystals

et al. 2023

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Section: Introductionmentioning

confidence: 99%

Manipulating D–A interaction to achieve stable photoinduced organic radicals in triphenylphosphine crystals

et al. 2023

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“…As shown in Figure 1D, TPA‐DHPy‐Py exhibited the lowest oxidation potential ( E ox = +0.486 V versus Fc/Fc + ) compared to those of TPA‐DHPy, TPA‐DHPy‐NT, TPA‐BTT‐DHPy, and TPA‐BTP‐DHPy ( E ox = +0.529–0.613 V versus Fc/Fc + ), revealing that TPA‐DHPy‐Py can more easily undergo oxidation reactions (Figure S34, Supporting Information). [ 23 ] The oxidative dehydrogenation transformation was further assessed using methylene blue (MB) as a photocatalyst in photoredox reactions due to high singlet oxygen ( 1 O 2 ) generation ability. [ 24 ] With 10 µ m MB and 660 nm laser, the TPA‐Py‐Py generated via oxidative dehydrogenation of TPA‐DHPy‐Py reached a higher yield (59.2%) than that of TPA‐Py (21.5%) upon laser irradiation for 5 min (Figure 1E).…”

Section: Resultsmentioning

confidence: 99%

The Golden Touch by Light: A Finely Engineered Luminogen Empowering High Photoactivatable and Photodynamic Efficiency for Cancer Phototheranostics

Chen

Zhang

et al. 2022

Adv Funct Materials

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Photoactivatable agent is a powerful tool in biomedicine studies due to highprecision spatiotemporal control of light. However, those previously reported agents generally suffer from short wavelength, fluorescence self-quenching effect, and the lack of photosensitizing property, which severely restrict their practical applications. To address these issues, molecular engineering of 1,4-dihydropyridine derivatives is conducted to obtain an optimized agent, namely TPA-DHPy-Py, which exhibits low oxidation potential, high photoactivation efficiency, and excellent type I/II combined photodynamic activity. Concurrently, its photoactivated counterpart is featured by aggregation-induced near-infrared emission and remarkable reactive oxygen species (ROS) production efficiency. Upon photoactivation, TPA-DHPy-Py is capable of precisely identifying cancer cells from co-culturing cancer cells and normal cells without the assistance of any extra targeting units, and in situ monitoring lipid droplets and endoplasmic reticulum alteration under ROS stress, as well as achieving fluorescent visualization of tumor in vivo with supremely high imaging contrast. Furthermore, the unprecedented performance on photodynamic cancer therapy is demonstrated by the significant inhibition of tumor growth. Therefore, the photoactivatable TPA-DHPy-Py with dual-organelle-targeted and excellent photodynamic activity associated with self-monitoring ability is highly promising for cancer theranostics in clinical trials.

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“…Recently, we found that the 2,5‐dimethyl pyrroles can be directly oxidized into red‐to‐NIR emissive radical cations, but they need to be stabilized by supramolecular host CB[7] in water solution [5] . To facilitate the theranostic applications, it's highly desirable to develop water‐stable radical cations without the assistance of supramolecular hosts.…”

Section: Methodsmentioning

confidence: 99%

A Water‐Stable and Red‐Emissive Radical Cation for Mutp53 Cancer Therapy

Zhou

Qian

et al. 2022

Angew Chem Int Ed

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Compared with conventional closed-shell fluorophores, radical cations provide an opportunity for development of red-to-NIR fluorophores with small sizes and easy preparation. However, most radical cations reported in the literature suffer from poor stability in water solution and are almost non-emissive. To tackle this challenge, we herein develop a deep-redemissive and water-stable pyrrole radical cation P * + À DPAÀ Zn, which can be easily generated from PÀ DPAÀ Zn by air oxidation. The deep-red-emissive P * + À DPAÀ Zn can be used for imaging-guided mitochondria-targeted delivery of Zn 2 + into cancer cells to promote mutant p53 proteins degradation and abrogate mutp53-manifested gain of function, including reduced chemotherapy resistance, inhibited cancer cell migration, decreased tumor cell colony and sphere formation. The water-stable and deep-red emissive pyrrole radical cation is thus promising for cancer theranostic applications.Red-to-NIR fluorescence imaging has significant advantages in terms of high penetration ability and less interference from autofluorescence. However, most of current redto-NIR fluorophores, such as cyanine and squaraine derivatives, are featured with complicated structures and suffer from difficulties for further decoration with therapeutic

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Red-to-NIR emissive radical cations derived from simple pyrroles

Abstract: Red-to-near-infrared (NIR) fluorophores are highly desirable in bio-imaging study with advantages of high tissue penetration ability and less interference from auto-fluorescence. However, their preparation usually requires tedious synthetic procedures, which...

Cited by 28 publications

References 47 publications

Manipulating D–A interaction to achieve stable photoinduced organic radicals in triphenylphosphine crystals

Manipulating D–A interaction to achieve stable photoinduced organic radicals in triphenylphosphine crystals

The Golden Touch by Light: A Finely Engineered Luminogen Empowering High Photoactivatable and Photodynamic Efficiency for Cancer Phototheranostics

A Water‐Stable and Red‐Emissive Radical Cation for Mutp53 Cancer Therapy

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