Electron‐Donating and Electron‐Withdrawing Subunit Effects on Coumarin‐BODIPY Dyads: Optical and Electrochemical Properties and Molecular Interactions

Köksoy, Baybars; Özdemir, Mücahit; Altınışık, Sinem; Zorlu, Yunus; Yalçın, Bahattin; Durmuş, Mahmut; Koyuncu, Sermet

doi:10.1002/cptc.202300043

Cited by 2 publications

(4 citation statements)

References 54 publications

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“…However, the coumarin ring is planar, and the dihedral angle is less than 1.0°. The single-crystal XRD data of coumarins obtained by Altınışık et al and Köksoy et al are in agreement with the DPP-Et-Kum-Et and DPP-Kum-Me-Me crystal data in this study. , …”

Section: Resultsmentioning

confidence: 99%

Coumarin–Phosphazenes: Enhanced Photophysical Properties from Hybrid Materials

Şahin,

Biryan,

Çalışkan

et al. 2024

Inorg. Chem.

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Phosphazenes have drawn a great deal of interest over the past 20 years as a potentially useful building block for the fabrication of fluorescent materials. The main objective of this work is to explore novel derivatives produced by coumarins, a class of chemicals well-known for their photophysical importance, and cyclophosphazenes. UV absorbance, fluorescence emission, quantum yield, and lifetime measurements were conducted to comprehend the optical properties. Furthermore, single-crystal X-ray analysis and theoretical calculations were carried out to confirm the structure of the molecule. The obtained findings collectively confirm the commendable optical properties exhibited by the studied compounds. Moreover, a detailed study of the crystal packing arrangement of DPP-Et-Kum-Et compound crystallized in the P21/n monoclinic space group revealed the presence of stacking interactions between the nonplanar conjugated benzene rings of the coumarins and the rigid diphenyl groups attached to the phosphazene ring. The crystal structure of the DPP-Kum-Me-Me compound is mainly based on classical C–H···O intermolecular hydrogen bonding interactions with an average distance of 2.52 Å. Importantly, the calculated absorption spectra of the compounds are in close agreement with the experimental data, further supporting their interesting electronic properties. Given that the DPP-Et-Kum-Et and DPP-Kum-Et compounds have the theoretically lowest band gaps (4.31 and 4.30 eV, respectively), the activation energies of these compounds were determined by an impedance analyzer using dc conductance values measured at different temperatures. The calculated activation energies for DPP-Et-Kum-Et and DPP-Kum-Et are 104.49 and 100.92 meV, respectively. The results demonstrate that both theoretical and experimental calculations are in agreement with each other and that the DPP-Kum-Et compound has the lowest conductivity.

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Section: Resultsmentioning

confidence: 99%

Coumarin–Phosphazenes: Enhanced Photophysical Properties from Hybrid Materials

Şahin,

Biryan,

Çalışkan

et al. 2024

Inorg. Chem.

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“…[23] The hybrid fluorophore was created by integrating xanthene and hemicyanine into an olefinic bond (Figure 2). [33] [24][25][26][27][28][29] and enable fluorescence off-on switching mode. These hybrid fluorophores were called "Changsha".…”

Section: Xanthene-cyanine Conjugated Hybrid Fluorophoresmentioning

confidence: 99%

“…Another example involves the fusion of xanthene and coumarin fluorophores, resulting in hybrid fluorophores with a large Stokes shift akin to that of coumarin fluorophores, while extending the emission wavelength based on xanthene fluorophores (Figure 1b). [25][26][27][28][29][30] Furthermore, hybrid fluorophores have found extensive applications in the fields of biological imaging, detection, therapy and other related areas. For instance, Hu et al designed a cyanine-coumarin hybrid fluorophore as a ratiometric fluorescent probe for accurate detection of peroxynitrite in mitochondria.…”

Section: Introductionmentioning

confidence: 99%

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Rational Design and Biological Application of Hybrid Fluorophores

Zhang,

Qu,

Zhang

et al. 2024

Chemistry A European J

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Fluorophores are considered powerful tools for not only enabling the visualization of cell structures, substructures, and biological processes, but also making for the quantitative and qualitative measurement of various analytes in living systems. However, most fluorophores do not meet the diverse requirements for biological applications in terms of their photophysical and biological properties. Hybridization is an important strategy in molecular engineering that provides fluorophores with complementarity and multifunctionality. This review summarizes the basic strategies of hybridization with four classes of fluorophores, including xanthene, cyanine, coumarin, and BODIPY with a focus on their structure‐property relationship (SPR) and biological applications. This review aims to provide rational hybrid ideas for expanding the reservoir of knowledge regarding fluorophores and promoting the development of newly produced fluorophores for applications in the field of life sciences.

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Electron‐Donating and Electron‐Withdrawing Subunit Effects on Coumarin‐BODIPY Dyads: Optical and Electrochemical Properties and Molecular Interactions

Cited by 2 publications

References 54 publications

Coumarin–Phosphazenes: Enhanced Photophysical Properties from Hybrid Materials

Coumarin–Phosphazenes: Enhanced Photophysical Properties from Hybrid Materials

Rational Design and Biological Application of Hybrid Fluorophores

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