Study of the fluorescence of perylene cation radical salts with a near field optical setup

Micheletto, Ruggero; Matsui, Jun; Yoshimatsu, Nobuki; Oyama, Munetaka; Okazaki, Satoshi

doi:10.1007/s00396-002-0739-3

Cited by 5 publications

(2 citation statements)

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“…19,20 While most radicals have a non-degenerate SOMO (single occupied molecular orbital), in the case of ion-radicals, precisely because of the presence of the charge, there is almost always delocalization of both spin and charge, a situation which completely changes the scope for the prediction of uorescence. Actually, a few studies have shown that benzoquinone anion-radicals, 21 or perylene cation-radicals, 22 indeed exhibit some uorescence, albeit with quite a low yield and which is only measurable at low temperature. Fluorescence has also been recorded from the very stable cation-radical derived from dihydrodimethylphenazine, 23 this time at room temperature, but again with a low yield (0.001).…”

Section: Electrouorochromic Molecules and Materialsmentioning

confidence: 99%

Electrofluorochromism: from molecular systems to set-up and display

2013

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Electrofluorochromism deals with electrochemical monitoring of luminescence features. There are several reasons to be interested in that field. The first one is the design of displays working in a similar way to electrochromic devices, substituting colors due to absorption with colors due to emission, thus producing much higher brilliance. This requires designing smart molecules and materials, which are likely to exhibit reversible switch of emission by controlling their redox state. There are also a lot of analytical applications, especially in biochemical issues, where in situ dual detection of electrochemical and fluorescence signals can lead to very sensitive and selective biosensors. To achieve this goal, instrumental developments are necessary, involving, among others, beyond diffraction limit and single molecule detection optical techniques. This paper reviews the most recent developments in the above mentioned fields of fluorescence spectroelectrochemistry, coupled detection of fluorescence and electrochemical signals and design of molecules and materials exhibiting electrofluorochromic properties. The first part describes the required features for molecular systems to exhibit a reversible switch in their luminescence properties according to a change in their redox state. Examples among organic and organometallic dyes and redox labelled fluorophores are listed. The second part focuses on the instrumental development in fluorescence spectroelectrochemistry and recent coupling of electrochemical techniques with fluorescence microscopy.Finally, some applications and devices are presented in the last part of this review. This should give an overview of this emerging research field at the interface between physics, chemistry and biology.

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Section: Electrouorochromic Molecules and Materialsmentioning

confidence: 99%

Electrofluorochromism: from molecular systems to set-up and display

2013

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“…In comparison, (2,6-diisopropylphenyl)-3,4-perylenedicarboxylic imide demonstrates oxidation at 1.37 V (vs SCE) and reductions at −1.10 and −1.66 V (vs SCE) . More comprehensive information about electrochemical properties of different NDI molecules/complexes can be found elsewhere. − In terms of materials preparation, it is worth noting the synthesis of cation-radical salts through the electrochemical oxidation of perylene dyes. − The I – /I 2 couple potential is 0.638 V (at 0 ionic strength and CH 3 CN) …”

Section: Resultsmentioning

confidence: 99%

Noncovalent Dualism in Perylene-Diimide-Based Keggin Anion Complexes: Theoretical and Experimental studies

Popova,

Kulik,

Samoilova

et al. 2023

Inorg. Chem.

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We report the synthesis and comprehensive characterization of organic−inorganic hybrid salts formed by bis-cationic N,N′-bis(2-(trimethylammonium)ethylene)perylene-3,4,9,10-tetracarboxylic acid bisimide (PTCD 2+ ) and Keggin-type 3) were structurally characterized by single crystal X-ray diffraction. The cations in both structures exhibited infinite chainlike arrangements through π−π interactions, contrasting with the previously reported cation−anion stacking observed in naphthalene diimide derivatives. A detailed theoretical study employing topological analysis of the electron density distribution within the quantum theory of atoms in molecules approach provided further insights into this structural dualism. Atomic force microscopy analyses revealed the formation of self-assembled supramolecular structures on graphite from molecular monolayers (3 nm of thick) to submicrometer aggregates for 2. Hyperspectral Raman spectroscopy imaging revealed that such heterostructures are likely formed by an enhanced π−π interactions. Both complexes demonstrated interesting electrochemical behavior, photoluminescence and Xray-induced luminescence. Electron spin resonance analysis confirmed charge separation in both compounds, with enhanced efficiency observed in compound 2. Our findings of these perylene-based organic−inorganic hybrid salts offer the potential for their application in optoelectronic devices and functional materials.

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