Tuning the formation of reductive species of perylene-bisimide derivatives in DMF via aggregation matter

Kang, Rui; Miao, Rong; Qi, Yanyu; Chang, Xingmao; Shang, Congdi; Wang, Li; Fang, Yu

doi:10.1039/c7cc05645a

Cited by 12 publications

(11 citation statements)

References 40 publications

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“…In donor solvents such as DMSO, the photochemical reduction of pPDIp is probably facilitated by the interactions of bulk solvent with the hydrogen of the aromatic pPDIp ring. Similar behavior has been recently observed for PDI and NDI modified derivatives ,…”

Section: Resultssupporting

confidence: 89%

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺

et al. 2018

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This study reports the influence of the medium on the aggregation processes of the complex [Ru(phen) 2 (pPDIp)] 2 + (phen = 1,10-phenanthroline; pPDIp = a bis-phenanthroline-substituted perylene diimide)and its consequences for the photochemical and photophysical properties of the system. Photolysis leads, initially, to emission of both chromophores: Triplet metalto-ligand charge transfer ( 3* MLCT; Ru, dp!phen, p*) and singlet intraligand charge transfer ( 1* ILCT; pPDIp, p! p*). However, the medium induces increased p-p intermolecular interactions that lead to the generation of a pPDIp * À moietyin DMSO, pPDIp * À (518 nm) and pPDIp * À and pPDIp 2À (420 nm) in the cell culture medium RPMI, and 3* pPDIp in buffer (pH 7.4) and starch films. The complex activates singlet oxygen in buffer solution without oxygen bubbling and under green light irradiation (dose = 0.41J/cm 2 ; [ 1 O 2 ] = 0.03-0.47 mmol L À1 for [Ru(phen) 2 (pPDIp)] 2 + = 10-150 mmol L À1 ). No cytotoxic effects on B16F10-Nex2 murine melanoma cell viability were observed up to a concentration of 10 mmol L À1 of complex. However, under green LED illumination (dose = 0.41 J/cm 2 ) the complex exhibits a strong photocytotoxic effect, displaying IC 50 = 1.2 mmol L À1 .

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Section: Resultssupporting

confidence: 89%

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺

et al. 2018

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“…Most anionic PDI species are readily reoxidized upon exposure to air 16–26 . To evaluate the stability of Zr-PDI •− , we kept TEA-loaded Zr-PDI •− under ambient conditions (open air and laboratory light) or at different temperatures.…”

Section: Resultsmentioning

confidence: 99%

“…PDI •− have already been used to regulate the balance of bacterial flora 13–15 . However, these applications, especially NIR photothermal conversion, are adversely affected by the instability of the RAs under ambient conditions 16–26 . The formation and use of ambient stable PDI •− thus remain of prime importance.…”

Section: Introductionmentioning

confidence: 99%

Stable radical anions generated from a porous perylenediimide metal-organic framework for boosting near-infrared photothermal conversion

et al. 2019

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Radical anions of electron-deficient systems are widely used, but are easily reoxidized upon exposure to air. Therefore, the stabilization of radical anions under ambient conditions is of great significance, but still remains a scientific challenge. Herein, perylenediimide is employed to prepare a crystalline metal-organic framework for stabilizing radical anions without extensive chemical modification. The porous, three-dimensional framework of perylenediimide can trap electron donors such as amine vapors and produce radical anions in-situ through photo-induced electron transfer. The radical anions are protected against quenching by shielding effect in air and remain unobstructed in air for at least a month. Because of the high yield and stability of the radical anions, which are the basis for near-infrared photothermal conversion, the framework shows high near-infrared photothermal conversion efficiency (η = 52.3%). The work provides an efficient and simple method towards ambient stable radical anions and affords a promising material for photothermal therapy.

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“…Perylene bisimide (PBI) is a very popular fluorophore due to its superior properties such as high fluorescence quantum yield, photochemical stability, and switchable emission between the monomeric state and the aggregated state. − PBI derivatives are proven to be effective for the sensing of hydrocarbons, such as alkylbenzenes and alkanes. − However, most of the PBI derivatives encounter poor solubility in common organic solvents and aggregation-caused quenching (ACQ) in the film state, due to the strong intermolecular π–π stacking. To overcome these drawbacks, structural modifications of the PBI provide an effective solution by introducing alkyl chains and nonplanar three-dimensional units, which, however, involve tedious organic synthesis. , …”

Section: Introductionmentioning

confidence: 99%

High-Performance NMHC Detection Enabled by a Perylene Bisimide-Cored Metallacycle Complex-Based Fluorescent Film Sensor

et al. 2021

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Non-methane hydrocarbons (NMHCs) can serve as precursors of ozone and photochemical smog, and hence their highly efficient detection is of great importance for air quality monitoring. Here, we synthesized a new fluorescent perylene bisimide (PBI)-cored metallacycle complex through coordinationdriven self-assembly and used it for the production of a fluorescent film sensor. The unique rectangular structure of the developed fluorophore endows the sensor with enhanced sensing performance and discriminability to n-alkanes (C 5−10 ). Specifically, the experimental detection limits for n-pentane, n-hexane, and ndecane are 39, 7, and 1.4 mg/m 3 , respectively, and the corresponding linear ranges are from 39 to 2546, 7 to 1745, and 1.4 to 85 mg/m 3 , respectively. Moreover, the sensing is fully reversible. In tandem with a gas chromatographic separation system, the film sensor showed comparable detection ability for the nalkanes with a commercial flame ionization detector (FID), while the film sensor needs no hydrogen; it occupies a much smaller size (30 × 30 × 44 mm 3 ) and consumes less energy (0.215 W). Further studies demonstrated that the developed sensor can be used for on-site and real-time quantification of NHMCs, laying the foundation for developing into a portable detector.

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Tuning the formation of reductive species of perylene-bisimide derivatives in DMF via aggregation matter

Abstract: Host-guest interaction and chemical modification are found to be effective in tuning the formation of reductive species of perylene-bisimide (PBI) derivatives in DMF. Moreover, some of the PBI derivatives as synthesized produce radical anions in the solvent without the need of a base.

Cited by 12 publications

References 40 publications

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺

Stable radical anions generated from a porous perylenediimide metal-organic framework for boosting near-infrared photothermal conversion

High-Performance NMHC Detection Enabled by a Perylene Bisimide-Cored Metallacycle Complex-Based Fluorescent Film Sensor

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Tuning the formation of reductive species of perylene-bisimide derivatives in DMF via aggregation matter

Abstract: Host-guest interaction and chemical modification are found to be effective in tuning the formation of reductive species of perylene-bisimide (PBI) derivatives in DMF. Moreover, some of the PBI derivatives as synthesized produce radical anions in the solvent without the need of a base.

Cited by 12 publications

References 40 publications

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)2(pPDIp)]2+

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)2(pPDIp)]2+

Stable radical anions generated from a porous perylenediimide metal-organic framework for boosting near-infrared photothermal conversion

High-Performance NMHC Detection Enabled by a Perylene Bisimide-Cored Metallacycle Complex-Based Fluorescent Film Sensor

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Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺

Influence of the Medium on the Photochemical and Photophysical Properties of [Ru(phen)₂(pPDIp)]²⁺