A novel coordination polymer of 7-azaindole-3-carboxylic acid with sodium ions: crystal and molecular structures, vibrational spectra and DFT calculations

Morzyk-Ociepa, Barbara; Szmigiel, Ksenia; Petrus, Rafał; Turowska‐Tyrk, Ilona; Michalska, Danuta

doi:10.1016/j.molstruc.2017.05.059

Cited by 14 publications

(3 citation statements)

References 44 publications

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“…It is known that organic acids can provide a stable associate (dimer, catemer, and bridged synthons, etc.) in solution using different non-covalent interactions [30][31][32][33]. Since the presence of a carboxyl group causes molecules to form various aggregates, in a continuation of our work on the design of a new effective fluorophore based on a 1,2,3-triazole core, we should evaluate the extent of their ability to form NCIs [34][35][36][37][38].…”

Section: Introductionmentioning

confidence: 99%

Combined NMR Spectroscopy and Quantum-Chemical Calculations in Fluorescent 1,2,3-Triazole-4-carboxylic Acids Fine Structures Analysis

Safronov

Kostova

Palafox

et al. 2023

IJMS

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The peculiarities of the optical properties of 2-aryl-1,2,3-triazole acids and their sodium salts were investigated in different solvents (1,4-dioxane, dimethyl sulfoxide DMSO, methanol MeOH) and in mixtures with water. The results were discussed in terms of the molecular structure formed by inter- and intramolecular noncovalent interactions (NCIs) and their ability to ionize in anions. Theoretical calculations using the Time-Dependent Density Functional Theory (TDDFT) were carried out in different solvents to support the results. In polar and nonpolar solvents (DMSO, 1,4-dioxane), fluorescence was provided by strong neutral associates. Protic MeOH can weaken the acid molecules’ association, forming other fluorescent species. The fluorescent species in water exhibited similar optical characteristics to those of triazole salts; therefore, their anionic character can be assumed. Experimental 1H and 13C-NMR spectra were compared to their corresponding calculated spectra using the Gauge-Independent Atomic Orbital (GIAO) method and several relationships were established. All these findings showed that the obtained photophysical properties of the 2-aryl-1,2,3-triazole acids noticeably depend on the environment and, therefore, are good candidates as sensors for the identification of analytes with labile protons.

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Section: Introductionmentioning

confidence: 99%

Combined NMR Spectroscopy and Quantum-Chemical Calculations in Fluorescent 1,2,3-Triazole-4-carboxylic Acids Fine Structures Analysis

Safronov

Kostova

Palafox

et al. 2023

IJMS

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“…This is also characteristic of related compounds. [18][19][20] The distance between the sodium atoms in dimer 2 is 2.7371(17) Å. This value slightly exceed the Na…Na distances in the complexes where sodium atoms are connected only due to two μ 2 -OPhbridging fragments (2.955-3.326 Å).…”

Section: Resultsmentioning

confidence: 91%

Synthesis, Structure and Luminescent Properties of Rare‐Earth‐Metal Oxyacridinates

et al. 2021

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Complexes of Sc, La, Sm, Gd, Tb and Yb with 1,3-di-tert-butyl-7methylacridin-4-olate (Acr Me ) and 1,3-di-tert-butyl-7-bromoacridin-4-olate (Acr Br ) ligands were obtained by reactions of respective acridinols with cyclopentadienides or tris (trimethylsilyl)amides of rare earth metals or by metathesis of metal chlorides with Na(Acr R ). The Sc and La complexes with Acr Me ligands revealed photo-and electroluminescence of moderate intensity while the Sm, Gd, and Tb complexes, as well as all complexes with Akr Br ligands, turned out to be luminescent inactive. The La(Akr Br ) 3 and Yb(Acr Br ) 3 complexes showed photovoltaic properties. The best results of energy conversion were achieved on three-layer model devices containing a lanthanum complex as a photoactive material.

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“…Azaindole and its metal complexes have been studied in development of novel catalysts, luminescent materials, and functionalized coordination polymers. [12][13][14][15] Therefore, investigations on the spectroscopic characteristics, photo-acidity and photo-stability of selective N-rich indole derivative is of great interest in chemistry, biology and pharmaceutical communities.…”

Section: Introductionmentioning

confidence: 99%

Laser spectroscopic characterization of supersonic jet cooled 2,6-diazaindole (26DAI)

Kalal,

Baweja,

Maity

2024

Preprint

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In this article, we present the laser spectroscopic investigation of a nitrogen rich indole derivative, 2,6-diazaindole (26DAI) in the gas phase for the first time. Laser induced fluorescence (LIF) and two-color resonant two-photon ionization (2C-R2PI) spectroscopies were carried out to understand the role of N-insertion on the electronic excitation of indole derivatives. The band origin for S1←S0 electronic transition was observed at 33915 cm-1, which was red shifted by 713 cm-1 and 1317 cm-1 from that of 7-azaindole and indole, respectively. The single vibronic level fluorescence (SVLF) spectroscopy of the molecule depicted a large Franck-Condon activity till 2500 cm-1 for ground state vibrational modes. The experimental vibrational frequencies from the SVLF spectrum were compared to Franck-Condon simulated frequencies at two different level of theories. The more accurate results were found at B3LYP-D4/def2-TZVPP, than the more energy demanding MP2/cc-pVDZ level. Fluorescence-dip infrared (FDIR) spectrum was recorded to determine the N-H stretching frequency of the molecule in the ground state, which was observed at 3524 cm-1. The photoionization efficiency spectroscopy was performed to measure the ionization energy of the molecule as 71866 cm-1, which is significantly higher as compared to 7-azaindole and indole. Thus, the above study suggests that the N-rich biomolecules appear to have a considerably lower risk of photodamage. The current investigation can shed light on to the nature’s way of stabilizing bio-relevant molecules with a possible N-insertion mechanism.

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A novel coordination polymer of 7-azaindole-3-carboxylic acid with sodium ions: crystal and molecular structures, vibrational spectra and DFT calculations

Cited by 14 publications

References 44 publications

Combined NMR Spectroscopy and Quantum-Chemical Calculations in Fluorescent 1,2,3-Triazole-4-carboxylic Acids Fine Structures Analysis

Combined NMR Spectroscopy and Quantum-Chemical Calculations in Fluorescent 1,2,3-Triazole-4-carboxylic Acids Fine Structures Analysis

Synthesis, Structure and Luminescent Properties of Rare‐Earth‐Metal Oxyacridinates

Laser spectroscopic characterization of supersonic jet cooled 2,6-diazaindole (26DAI)

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