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Anion Sensing by Novel Triarylboranes Containing Boraanthracene: DFT Functional Assessment, Selective Interactions, and Mechanism Demonstration Haamid Rasool Bhat, Parth Sarthi Sen Gupta, Satyaranjan Biswal, and Malay Kumar Rana* Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Government ITI Campus, Engineering School Road, Ganjam, Berhampur 760010, Odisha, India
ACS Omega 2019.4:4505-4518. Downloaded from pubs.acs.org by 94.231.218.221 on 03/03/19. For personal use only.
S Supporting Information *
ABSTRACT: Analytical methods often involve expensive instrumentation and tedious sample pretreatment for an analyte detection. Being toxic and detrimental to human health, sensing of cyanide (CN−), fluoride (F−), chloride (Cl−), bromide (Br−), nitrate (NO3−), acetate (CH3COO−), and bisulfate (HSO4−) is performed by a boron-based molecular receptor, N,N,N,3,5-pentamethyl-4-{2-thia-9boratricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,6,11,13-hexaen9-yl}anili-nium (1), and the three newly designed receptors from it. Thermodynamics, electronic structure, and photophysical properties are computed by employing density functional theory (DFT) and time-dependent density functional theory (TD-DFT) to explore selective sensing of these anions and its mechanism. Free-energy changes (ΔG) and binding energies (ΔE) suggest that among these anions, only binding of CN− and F− is thermodynamically feasible with a very strong binding affinity with the receptors. Boron atoms containing positive natural charges act as the electrophilic centers to bind the anions involving a 2p−2p orbital overlap resulting in charge transfer. In the receptor−analyte complexes with CN− and F−, fluorescence is quenched due to the intramolecular charge transfer transitions (π−π* transitions in the case of the receptors lead to fluorescence), internal conversion, and associated configurational changes. Among the six tested functionals, CAM-B3LYP/6-31G(d) is found to be the most accurate one. The designed receptors are better fluorescent probes for F− and CN−, demonstrating their importance for the practical utility.
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INTRODUCTION The deadly poisonous nature of the cyanide ion (CN−) makes it very toxic to human body.1 The binding between CN− and heme unit of cytochrome c causes paralysis of the cellular respiration and ultimately leads to serious central nervous system damages.2,3 As the versatility of cyanide reagents in industry is depicted by their role in synthesis, metallurgy, etc., their release into the environment is unavoidable.4,5 On the other hand, fluoride (F−) has so many beneficial effects like treating osteoporosis, protection of dental health, etc. when consumed in a controlled manner.6,7 But fluoride overdose causes pathological disorders like skeletal and tooth fluorosis, kidney failure, urolithiasis, and may even lead to death.8−10 Thus, World Health Organization (WHO) has fixed the maximum permitted limit at 0.07 and 1.5 mg/L, respectively, for CN− and F− in drinking water.11,12 In connection to these facts and due to the continuous discharge of F− and CN− into the environment, the development of a method for the accurate trace-level quantification of these anions is indispensable. Although various analytical methods like potentiometry, absorption spectrometry, inductively coupled plasma emission spectrometry, etc. are used for detection of trace levels of F− and CN− and other anions ( 1) absorption transitions; emission occurs involving IC with a significant geometrical change to the receptor−analyte complexes unlike the emission of the receptors, which is conceived as the reason for the fluorescence quenching (f ∼ 0.0001−0.0006) upon anion binding. Natural population analysis, hybrids, and MO plots provide a clear picture of receptor−analyte interactions. The anions bind to the boron centers having partial positive charges, leading to change of hybridization from sp2 to sp3 in 1−4. Such interactions involve 2p−2p orbital overlap between the boron centers of the receptors and the anions accompanied by anion → receptor charge transfer, quantified in ΔQ. There is greater degree of charge transfer in the case of CN− (e.g., in 1CN, ΔQ = −0.6829) than F− (e.g., 1F, ΔQ = −0.4504), which may be because of the electronegativity difference between fluorine and the carbon of the cyanide analyte. Among the six different DFT functionals used, CAM-B3LYP gives the best accuracy to reproduce experimental data (geometries, absorption and emission peaks) for its augmented largest exact exchange component. The PES scanning validates the optimized geometries considered in the ground and excited states, 4515
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Parac noted a substantial failure while estimating excitation energies for lowest-lying π → π* states in oligoacenes by using standard hybrid functionals in TD-DFT (error > 0.5 eV).74 To address this unexpected and surprising failure of TD-DFT in these simple valence excitations, Wong and co-workers75,76 and Peng et al.77 showed that some range-separated functionals,78,79 which possess both an asymptotically correct contribution of Hartree−Fock (HF) exchange and a positiondependent admixture, yield significant improvements over the conventional hybrids in the excitations of oligoacenes and DNA complexes. They observed that all full-HF-exchange LC functionals gave similar results for the linear acenes upon employing several range-separated and LC functionals like CAM-B3LYP, LC-BOP, LC-PBE, LC-ωPBE, and LC-BLYP. The CAM-B3LYP functional as defined80 has a Coulombattenuating parameter of α + β = 0.65 and −0.65/r dependence for the exchange potential. Hence, the CAMB3LYP functional is principally different from other LC functionals considered in the work of Wong and Hsieh75 because at large interelectronic distances, it does not include a full 100% HF exchange. It is also found that the previously obtained systematic errors for the acene systems by Grimme and Parac74 is mainly due to the HF exchange component rather than the specific DFT correlation contribution used because similar results were obtained from other full-exchange LC functionals as well. As the CAM-B3LYP functional cannot capture the correct 100% asymptotic distance, it gives inaccurate results. Among all of the functionals employed herein, the CAM-B3LYP, however, has the highest exchange part (65% exchange and 35% correlation); thus, it gives the better accuracy and is more reliable comparatively. In both the ground and excited states, potential energy surface (PES) scanning was done along the angles over which maximum configurational change occurs in traversing from S0 to S1 state. It is worth mentioning that the configurations at the local minima of S0 and S1 potential energy surfaces are same as those of the corresponding optimized geometries attained at CAMB3LYP/6-31G(d), validating the structural choice of optimized ions and complexes given by this method. To take into account the effect of solvation in tetrahydrofuran (THF, ε = 7.58), conductor-like polarizable continuum model (CPCM) as implemented in Gaussian 09 was used in all of the calculations.81 Natural bond orbital (NBO) method using the NBO 3.1 version as implemented in Gaussian 09 program was exploited for performing the natural population analysis at the CAM-B3LYP/6-31G(d) level of theory.82 Binding energies (ΔE) and free-energy changes (ΔG) were calculated for complexes of 1, 2, 3, and 4 with the seven different anionic analytes considered herein with the following equations ΔE = Ecomplex − (Ereceptor + Eanion)
(1)
ΔG = Gcomplex − (Greceptor + Ganion)
(2)
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Tel: +916802227753. ORCID
Haamid Rasool Bhat: 0000-0003-3889-6044 Malay Kumar Rana: 0000-0002-1713-8220 Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS The authors acknowledge IISER Berhampur and IIT Kanpur for the computational support. H.R.B. also sincerely acknowledges IISER Berhampur for providing him the Institute Postdoc Fellowship to carry out this work. H.R.B is also thankful to Dr. Prakash Chandra Jha, Central University of Gujarat, Gandhinagar, India for important discussions and suggestions.
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where E and G refer to total energy and Gibbs free energy, respectively. For reducing the basis set superposition error (BSSE) in these energy terms, the Boys−Bernardi scheme was used to offer the counterpoise corrected energies.83
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Calculated geometrical parameters for the fully optimized structures of 1−4, 1F−4F, and 1CN−4CN in the ground and excited states and the corresponding X-ray data; excitation and de-excitation energies calculated by employing different functionals; ground-state optimized structures of 1F−4F, 1CN−4CN; excited-state optimized structures of 1−4, 1F−4F, and 1CN−4CN; potential energy curves of the ground and excited states of 1F and 2CN; calculated FMOs and their corresponding energies involved in excitation and emission of 2−4, 2F−4F, and 2CN−4CN; molecular orbital diagrams of (I) 1, (II) F−, and (III) CN−; and schemes for the different mechanisms of fluorescence emission of 2−4, 2F−4F, and 2CN−4CN (PDF)
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