Molecular recognition of anthracene and indeno-pyridine by (dibenzoylmethanato)boron difluoride in ethanol

Chaudhuri, Tandrima; Salampuria, Sneha; Mukhopadhyay, Chhanda; Tapaswi, Pradip Kumar; Chattopadhyay, Subrata; Banerjee, Manas

doi:10.1016/j.jphotochem.2012.08.017

Cited by 14 publications

(7 citation statements)

References 17 publications

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“…Earlier, we observed electron donor-acceptor (EDA) interactions between the BF 2 -complex of dibenzoylmethane and some of the PAHs in alcoholic medium. 7 But PAH sensing via H-bonding with axial C-H proton of PAHs is not yet found in literature. The BF 2 -dipyrromethene (Bodipy) molecules ( Figure 1) pursuing research in chemistry and applications of the Bodipys.…”

Section: F Nmr Cyclic Voltametry Powder Xray and Monte Carlo Simulamentioning

confidence: 99%

“…Earlier, we observed electron donor-acceptor (EDA) interactions between the BF 2complex of dibenzoylmethane and some of the PAHs in alcoholic medium. 7 But PAH sensing via H-bonding with axial C-H proton of PAHs is not yet found in literature.…”

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confidence: 99%

“…The observed isosbestic dyes/PAH (1 : 2) adducts formation was also precisely explained by enhancement of uorescence quantum yield, IR, NMR, CV, powder X-ray and conformational searching studies of adducts. We have earlier 7 shown that electron-decient (dibenzoylmethanato) boron diuoride having a similar -BF 2 unit can efficiently sense electron-rich PAHs, D1-D3 in ethanol medium by simple p-p stacking, without any H-bonding type interaction. Thus, the present observation on the interaction in Bodipy-PAH system is unique, warranting further extension of the work for sensor applications.…”

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confidence: 99%

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Bodipy recognizes polyaromatic hydrocarbons via C–H⋯F type weak H-bonding

Chaudhuri¹,

Shivran

Mula

et al. 2016

RSC Adv.

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Section: F Nmr Cyclic Voltametry Powder Xray and Monte Carlo Simulamentioning

confidence: 99%

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Bodipy recognizes polyaromatic hydrocarbons via C–H⋯F type weak H-bonding

Chaudhuri¹,

Shivran

Mula

et al. 2016

RSC Adv.

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“…Some of these rely on the donor-acceptor concept using derivatives of boron or pyridine, for which calculated the binding constants. [9] Another approximation considers a binuclear complex of rhenium (I) with substituents like pincers, able to recognize PAHs in solution through charge transfer and CH-π interactions. [10] In 2004, Sánchez-Cortés group used the calix [4]arenes with different substituents in the lower rim for the selective recognition of PAHs, detecting the complexes with Surface-Enhanced Raman Scattering (SERS) spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Double Hook Perylene Diimide as a New Receptor for PAHs: An Experimental and Theoretical Study

et al. 2023

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In a one‐step reaction, we prepared a dibenzylamine perylene diimide derivative (PDI). Its double hook structure allows for self‐association with a constant of Kd ∼108 M−1 determined by fluorescence. We confirmed its ability to bind PAHs using UV/Vis, fluorescence, and 1H NMR titrations in CHCl3. The complex formation signature in UV/vis is a new band at 567 nm. The calculated binding constants (Ka∼104 M−1) follow the trend pyrene>perylene>phenanthrene>naphthalene>anthracene. Theoretical modeling of these systems using DFT ωB97X‐D/6‐311G(d,p) proved helpful in rationalizing the complex formation and the observed association trend. The distinctive signal in UV/vis is due to a charge transfer in the complex from orbitals in the guest to the host. SAPT(DFT) confirmed that the driving forces in the complex formation are exchange and dispersion (π–π interactions). Still, the recognition ability depends on the electrostatic component of the interaction, a minor fraction.

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“…In recent years, difluoroboron β-diketonates have attracted considerable attention due to their interesting and rich photophysical properties. In particular, (dibenzoylmethanato)boron difluoride (DBMBF2) and its derivatives have been used in several studies related to complexation with mono- and polyaromatic hydrocarbons in the ground and excited states, − solvatochromism, − room-temperature phosphorescence, , two-photon absorption, white light emission, etc.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Spectra of (Dibenzoylmethanato)boron Difluoride Exciplexes with Aromatic Hydrocarbons: A Theoretical Study

2015

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An approach is proposed for the quantum-chemical calculation of the structure and fluorescence spectra of exciplexes. The procedure involves the geometry optimization of exciplexes using the CIS method with empirical dispersion correction (CIS-D) and the subsequent single-point calculation of the transition energy using the CIS method with perturbative correction for double excitations (CIS(D)). Calculated fluorescence band positions for exciplexes of (dibenzoylmethanato)boron difluoride with substituted benzenes are in reasonable agreement with the experimental data.

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Molecular recognition of anthracene and indeno-pyridine by (dibenzoylmethanato)boron difluoride in ethanol

Cited by 14 publications

References 17 publications

Bodipy recognizes polyaromatic hydrocarbons via C–H⋯F type weak H-bonding

Bodipy recognizes polyaromatic hydrocarbons via C–H⋯F type weak H-bonding

Double Hook Perylene Diimide as a New Receptor for PAHs: An Experimental and Theoretical Study

Fluorescence Spectra of (Dibenzoylmethanato)boron Difluoride Exciplexes with Aromatic Hydrocarbons: A Theoretical Study

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