Solid-state fluorescence properties of small iminocoumarin derivatives and their analogues in the coumarin series

Abid-Jarraya, Nihel; Khemakhem, Kacem; Turki-Guermazi, Hamida; Abid, Souhir; Saffon, Nathalie; Fery–Forgues, Suzanne

doi:10.1016/j.dyepig.2016.04.039

Cited by 20 publications

(8 citation statements)

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“…2-Iminocoumarines are known to be a very important class of organic compounds due to their properties. Similar to the well-studied coumarines, which have been found in various species of plants, − 2-iminocoumarine derivatives are used as dyes , and fluorescent sensors for detection of metal ions in a very low concentration. − Furthermore, these fluorophores have low cytotoxicity and can selectively stain organelles in living cells . A lot of 2-iminocoumarines possess high antibacterial, antifungal, anti-HIV, antimicrobial, , anti-Alzheimer , activity.…”

Section: Introductionmentioning

confidence: 99%

Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(N-(2-Fluorophenyl)imino)coumarin-3-carboxamide

et al. 2021

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Crystallization of concomitant polymorphs is a very intriguing process that is difficult to be studied experimentally. A comprehensive study of two polymorphic modifications of acetyl 2-(N-(2-fluorophenyl)imino)coumarin-3-carboxamide using quantum chemical methods has revealed molecular and crystal structure dependence on crystallization conditions. Fast crystallization associated with a kinetically controlled process results in the formation of a columnar structure with a nonequilibrium molecular conformation and more isotropic topology of interaction energies between molecules. Slow crystallization may be considered as a thermodynamically controlled process and leads to the formation of a layered crystal structure with the conformation of the molecule corresponding to local minima and anisotropic topology of interaction energies. Fast crystallization results in the formation of a lot of weak intermolecular interactions, while slow crystallization leads to the formation of small amounts of stronger interactions.

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Section: Introductionmentioning

confidence: 99%

Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(N-(2-Fluorophenyl)imino)coumarin-3-carboxamide

et al. 2021

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“… Attributed to the herringbone arrangement with a slipped stacked, or parallel head-to-tail array, another series of related coumarins ( 32d – 32f , Scheme ) was reported by Fery-Forgues and co-workers. These compounds displayed moderate QYs from Φ F = 33% to Φ F = 87% in solution and Φ F = 5% to Φ F = 26% in the solid state …”

Section: Classification Of Dual-state Emission Compounds: Frequent Mo...mentioning

confidence: 99%

Dual-State Emission (DSE) in Organic Fluorophores: Design and Applications

et al. 2021

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Organic luminescent materials have attracted significant attention in the past few years due to their fascinating photophysical properties. Implementing these emissive organic compounds is now being actively pursued in many applications in solution (i.e., sensors, bioimaging) or their solid forms (i.e., optoelectronic devices or data encryption). Despite significant advances in the development of emissive compounds, there has been an increasing quest in the past decade for materials where the emission is preserved in both states, dual-state emission (DSE). These compounds are expected to detonate a myriad of applications in the future. On this nascent topic, this work addresses several factors that increase the probability of obtaining the dual-state emission property based on the precedent reports showing this phenomenon. Therefore, this review identifies and organizes the different structural characteristics useful to obtain these compounds. In addition, it has been devised to motivate the discussion in the materials science community and hopefully incentivize the efforts of many research groups around the world toward the synthesis of new dual-state emitters.

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“…CCDC 2108110 and 2108116. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2qm00067a tetraphenylethene (TPE), 19,20 triphenylamine, 21,22 cyanostilbene, 23 coumarin, 24 perylene diimides (PDIs), 25 carbazole, 26 and a few others, [27][28][29] so far have been reported to serve as scaffolds for engineering DSEgens. Navigation into the molecular structures reveals the critical importance of the delicate balance between the twisting conformation and rigid conjugation to achieve the DSE.…”

Section: Introductionmentioning

confidence: 99%