Accessing the Triplet State in Heavy‐Atom‐Free Perylene Diimides

Yu, Zhenyi; Wu, Yishi; Peng, Qian; Sun, Chun‐Lin; Chen, Jianwei; Yao, Jiannian; Fu, Hongbing

doi:10.1002/chem.201600300

Cited by 79 publications

(90 citation statements)

References 28 publications

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“…As previously observed for other molecules, these results suggest that the population of the triplet excited state recorded could be induced by the non‐planar geometry of molecule 1 as proposed for similar core‐twisted PAHs. [ ][ ][ ] The corresponding lifetime of 1 at 1720 nm at 77 K appeared to be < 10 ns ( i.e . beyond the limit of the detector response of our detector).…”

Section: Resultsmentioning

confidence: 99%

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

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The preparation of the first soluble quaterrylene derivative featuring peripheral tert‐butyl substituents and sterically hindering, core‐anchored triflate groups has been achieved. This involves a facile synthetic route based on an oxidative coupling of perylene precursors in the presence of H2O2 as oxidant. The steric hindrance between the TfO substituents at the central bay position of the quaterrylene board triggers a strong deformation of the central perylene planarity, which forces the quaterrylene platform to adopt a twisted geometry as shown by X‐ray analysis. Exceptionally, photophysical investigations show that the core‐twisted quaterrylene phosphoresces in the NIR spectral region at 1716 nm. Moreover, third‐order nonlinear optical measurements on solutions and thin film containing the relevant molecule showed very large second hyperpolarizability values, as predicted by theoretical calculations at the CAM‐B3LYP/6‐31G** level of theory, making this material very appealing for photonic applications.

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Section: Resultsmentioning

confidence: 99%

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

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“…The value of k ISC can be greatly promoted by smaller Δ E ST and effective spin–orbit coupling (SOC) between singlet and triplet states. It is reported that a pronounced ICT character may serve to decrease Δ E ST ; thus the donor–accepter (D‐A) molecular design strategy is useful for metal‐free organic molecular modification in RTP and thermally activated delayed fluorescence (TADF) materials . Heavy halogen atoms (i.e., I and Br) can also trigger significant SOC .…”

Section: Factors Governing Rtpmentioning

confidence: 99%

Enhanced Room‐Temperature Phosphorescence through Intermolecular Halogen/Hydrogen Bonding

Xiao

2018

Chemistry A European J

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130

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Room-temperature phosphorescence (RTP) materials with high efficiency have attracted much attention because they have unique characteristics that cannot be realized in conventional fluorescent materials. Unfortunately, efficient RTP in metal-free organic materials is very rare and it has traditionally been considered as the feature to divide purely organic compounds from organometallic and inorganic compounds. There has been increasing research interest in the design and preparation of metal-free organic RTP materials in recent years. It has been reported that intermolecular interactions make a big difference to the photophysical behavior of organic molecules. In this regard, herein, the parameters that affect RTP efficiency are discussed, and a brief review of recent intermolecular halogen-/hydrogen-bonding strategies for efficient RTP in metal-free organic materials are provided. The opportunities and challenges are finally elaborated in the hope of guiding promising directions for the design and application of RTP materials.

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“…This might include generation of singlet oxygen, and subsequent pollutant degradation and photodynamic activity [7,10,15]. A number of perylene-3,4,9,10-tetracarboxylic acid (diimide) derivatives, known as PDIs, and polypyridine complexes derived from perylenes have shown good results in the production of reactive species of reactive oxygen species (ROS) [11,[16][17][18]. The ligands containing the perylene moiety are reddish dyes with very high quantum yields of luminescence.…”

Section: Omentioning

confidence: 99%

“…The ability to produce singlet oxygen depends largely on the production of a long-lived triplet state, [13,14,17,18] and the moderate quantum yield values of 1 O 2 and the high absorbance of the perylene moiety in the visible range make cis-[Ru (phen) 2 (pPDI)] 2+ a possible photosensitizer to be used in water disinfection or other singlet oxygen-base processes that use sunlight as an excitation source. Since the Ru complex has a long-lived triplet state, it is of possible that in addition to formation of singlet oxygen, formation of superoxide anion by electrontransfer processes and/or Type I photooxidation processes take place upon irradiation of the Ru complex under aerobic conditions.…”

Section: Singlet Oxygen Measurements à Efficiency Of Singlet Oxygen Pmentioning

confidence: 99%

Singlet oxygen production by a polypyridine ruthenium (II) complex with a perylene monoimide derivative: A strategy for photodynamic inactivation of Candida albicans

Maia

Aguiar

Velloso

et al. 2018

Journal of Photochemistry and Photobiology A: Chemistry

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We report the synthesis, optical, electrochemical and electronic properties of a new perylene derivative and its Ru(II) complex, namely N,-(5-amino-1,10-phenantroline)perylene-3,4,9,10-tetracarboximonoimide (pPDI) and Bis(1,10-phenanthroline)(N-(5-amin-1,10-phenantroline)perylene-3,4,9,10-tetracarboxi monoimide)ruthenium(II) hexafluorophosphate, [Ru(phen) 2 (pPDI)] 2+ ([PF 6 ] À) 2. The molecular structures of the compounds were elucidated by FTIR, mass spectrometry, elemental analysis (CHN) and DFT calculations. Their optical and electrochemical properties were investigated by absorption and fluorescence spectroscopy and cyclic voltammetry. The spectroscopic and electrochemical studies for both the pPDI and the perylene monoimide metal complex show that Ru 2+ coordination does not affect the optical and electrochemical properties of the free perylene bisimide ligand. The Ru complex exhibits emission lifetimes of 5.06 ns (48.1%) and 156 ns (51.9%), resulting from emission of the pPDI ligand and 3 MLCT, respectively. The pPDI triplet excited state in the title chromophore is able to sensitize the production of singlet oxygen (1 O 2). Using a time-resolved laser system, we measured the quantum yield for the production of singlet oxygen (FD) to be 0.26 for cis-[Ru(phen) 2 (pPDI)] 2+. Candida albicans is recognized as the most common fungal pathogens, causing superficial infections of the skin and mucous membranes. Resistance of C. albicans strains against classical antifungal agents such as fluconazole has increased considerably, which drives the search for new therapeutic alternatives. In the present study, we report that our new Ru-perylene complex can indeed be used to kill the bacterium C. albicans. The fungicidal activity of cis-[Ru(phen) 2 (pPDI)] 2+ against C. albicans was evaluated in the presence of C. albicans cultures in the dark and in the presence of light. After exposure to 12.5 mM of cis-[Ru (phen) 2 (pPDI)] 2 in the presence of light for 180 s, C. albicans showed a decrease of 50% in its concentration compared to the same experimental conditions in the dark.

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Accessing the Triplet State in Heavy‐Atom‐Free Perylene Diimides

Cited by 79 publications

References 28 publications

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Enhanced Room‐Temperature Phosphorescence through Intermolecular Halogen/Hydrogen Bonding

Singlet oxygen production by a polypyridine ruthenium (II) complex with a perylene monoimide derivative: A strategy for photodynamic inactivation of Candida albicans

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