Optical properties of V-shaped bis-coumarins: Ab initio insights

Budzák, Šimon; Charaf-Eddin, Azzam; Medveď, Miroslav; Gryko, Daniel T.; Jacquemin, Denis

doi:10.1016/j.comptc.2015.12.001

Cited by 10 publications

(3 citation statements)

References 58 publications

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“…As an example, in bis-phenol 7 both absorption and emission maxima were shifted bathochromically when moving from nonpolar to polar solvents (Figure ). Solvatochromism displayed by 1-oxapyren-2-ones can be explained by the charge-transfer character of the optical transition. ,, In nonpolar media (toluene, CH 2 Cl 2 ), the absorption spectra showed only short-wavelength band around 430 nm. However, with an increase in the solvent polarity (MeOH, DMSO), a second absorption band appeared at 503 and 520 nm, respectively.…”

Section: Resultsmentioning

confidence: 99%

Vertically π-Expanded Coumarins: The Synthesis and Optical Properties

2016

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A regioselective synthesis of naphtho[2,1,8-def]coumarins has been realized through a concise route that involves the intramolecular Friedel-Crafts reaction of benzo[f]coumarins. Tetracyclic, planar products were prepared starting from assembly of the suitably substituted coumarin via the Pechmann reaction of 2-naphthols with acetone-1,3-dicarboxylates, followed by an intramolecular Friedel-Crafts reaction. In contrast to earlier report, the main product of the condensation reaction performed at 130 °C was the corresponding sulfonic acid and not the phenol itself. The one-pot process afforded the desired phenol in 39% yield. This reaction has been extended to some naphthalenediols. The model 5-hydroxy-naphtho[2,1,8-def]coumarin was transformed into corresponding dimer using various pathways including intermolecular oxidative aromatic coupling. Photophysical studies revealed that 5-hydroxy-naphtho[2,1,8-def]coumarin has the most bathochromically shifted both absorption and emission among all π-expanded coumarins bearing one OH functionality. In general, all prepared coumarin-phenols as well as their hexyl ethers displayed moderate to strong greenish-yellow fluorescence, except of dimer that emits at 552 nm. The fluorescence of these dyes was strongly dependent on polarity of the solvent. Computational studies supported interpretation of optical properties for the selected compounds.

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Section: Resultsmentioning

confidence: 99%

Vertically π-Expanded Coumarins: The Synthesis and Optical Properties

2016

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“…Coumarins are highly fluorescent chromophores ( Katerinopoulos, 2004 ). They are easy to synthesize, chemically stable, and are characterized by generally high quantum yields ( Budzák et al, 2016 ). Novel therapeutic approaches, such as photodynamic therapy (PDT), involve the application of photosensitizing transition metal complexes with optically active ligands ( Teo et al, 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Coumarin-transition metal complexes with biological activity: current trends and perspectives

Todorov,

Kostova

2024

Front. Chem.

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Coumarin (2H-1-benzopyran-2-one) presents the fundamental structure of an enormous class of biologically active compounds of natural, semi-synthetic, and synthetic origin. Extensive efforts are continually being put into the research and development of coumarin derivatives with medicinal properties by the broad scientific community. Transition metal coordination compounds with potential biological activity are a “hot topic” in the modern search for novel drugs. Complexation with transition metals can enhance the physiological effect of a molecule, modify its safety profile, and even imbue it with novel attributes of interest in the fields of medicine and pharmacy. The present review aims to inform the reader of the latest developments in the search for coumarin transition metal complexes with biological activity, their potential applications, and structure-activity relationships, where such can be elucidated. Each section of the present review addresses a certain kind of biological activity (antiproliferative, antioxidant, antimicrobial, etc.), explores the most recent discoveries in the field, and, at the same time, tries to offer useful perspectives for potential future investigations.

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“…[19][20][21][22][23] Heterocycle-fused coumarin derivatives with the p-extended conjugation systems possess promising photophysical properties in comparison with the simple coumarin derivatives. [24][25][26][27][28][29][30] Among the heterocycle-fused coumarins, V-shaped fused-biscoumarins have attracted significant attention due to their distinguished properties, such as bathochromic-shift in the emission and excitation wavelengths, colorimetric properties, and larger Stokes shift, [31][32][33][34][35] and the photophysical properties and applications of V-shaped fused-biscoumarins are strongly dependent on the fused coumarin ring systems. However, V-shaped fusedbiscoumarins have larger rigid conjugated planes in comparison with the simple coumarins, and they are more prone to forming strong intermolecular p-p stacking interactions in the aggregated state, resulting in aggregation-induced fluorescence quenching, which could limit their application in the field of organic optoelectronic devices.…”

Section: Introductionmentioning

confidence: 99%