scholarly journals New naphtho[1,8-ef]perimidines: synthesis, fluorescence studies and application for detection of nitroanalytes

2021 ◽  
Vol 8 (4) ◽  
pp. 20218416
Author(s):  
Igor L. Nikonov ◽  
Leila K. Sadieva ◽  
Мaria I. Savchuk ◽  
Еkaterina S. Starnovskaya ◽  
Dmitry S. Kopchuk ◽  
...  

A rational approach to the synthesis of substituted naphtho[1,8-ef]perimidines based on SNH methodology and cyclization  reaction in the series of condensed azines with naphthalene substituents was presented. Photophysical properties of the obtained fluorophores were studied, in particular, green fluorescence in the 485–536 nm range with quantum yield up to 32.4% was detected. HOMO-LUMO energy values and distributions for the new compounds were calculated by the DFT method in comparison with nitroanalytes and perylene. Based on the data obtained, as well as on the results of fluorescence titration, the possibility of using the new diazaperylenes as potential chemosensors for the visual detection of nitro-containing explosives was shown.

Author(s):  
Elham Abdalrahem Bin Selim ◽  
Mohammed Hadi Al–Douh ◽  
Hassan Hadi Abdullah ◽  
Dahab Salim Al–Nohey

Two bis-Schiff Bases 1 and 2 are ligands that can coordinate with manganese metal to form stable complexes and have biological activity. Thermodynamic parameters, HOMO-LUMO energy levels and FTIR spectra of two ligands have been computed using B3LYP/6-311++G(d,p) functional of the DFT calculations. Both ligands are favored thermodynamically, and the ligand 1 has been shown to be more stable than ligand 2. The Polarizability values of two ligands have been investigated. The results refer that ligand 2 interacts earlier than ligand 1 to the metal ion. The FTIR spectra of two ligands have been evaluated. All results show the good agreement between the theoretical and experimental data.


2006 ◽  
Vol 84 (4) ◽  
pp. 477-485 ◽  
Author(s):  
Wei-Hua Huang ◽  
Wen-Li Jia ◽  
Suning Wang

The syntheses of several new 7-azaindolyl-, indolyl-, and 3-methylindolyl-functionalized starburst molecules that contain either a 1,3,5-triazine, a benzene, a 2,4,6-triphenyl-2,4,6-triazine, a 1,3,5-triphenylbenzene, a 2,4,6-tris(biphenyl)-1,3,5-triazine, or a 1,3,5-tris(biphenyl)benzene core have been achieved. The synthetic methods used for these new compounds involve mostly Ullmann condensation and Suzuki coupling reactions. The thermal properties of the new molecules have been found to be highly dependent on the molecular weight and the central core. Glass transition temperatures greater than 150 °C were observed for the large starburst molecules based on the 2,4,6-tris(biphenyl)-1,3,5-triazine or the 1,3,5-tris(biphenyl)benzene core. The new starburst molecules are luminescent in the violet-blue region in solution and in the solid state. The emission energy and the quantum efficiency were found to be highly dependent on the central core and the functional group. In general, the triazine-based molecules were found to have a smaller HOMO–LUMO energy gap than the benzene-based analogues. The triphenyltriazine- or triphenylbenzene-based molecules were found to display a higher emission quantum efficiency than the large tris(biphenyl)triazine- or tris(biphenyl)benzene-based molecules.Key words: 7-azaindolyl, indolyl derivative, triazine and benzene cores, starburst molecule, blue luminescence.


2019 ◽  
Vol 23 (11n12) ◽  
pp. 1563-1569 ◽  
Author(s):  
Ebru Özkan Garip ◽  
Mukaddes Özçeşmeci ◽  
Ramazan Katırcı ◽  
İbrahim Özçeşmeci ◽  
Esin Hamuryudan

Unsymmetrical metal-free phthalocyanine was synthesized through cyclotetramerization of 4-[2,6-dimethyl-4-(4-tert-butyl-phenylazo)phenoxy]phthalonitrile and 4-(hexylthio)phthalonitrile in the presence of lithium in [Formula: see text]-pentanol, then metal-free phthalocyanine was obtained by acidification with acetic acid. Finally, metalation was achieved by refluxing metal-free phthalocyanine in [Formula: see text]-pentanol in the presence of zinc (II) salt. The structure of synthesized phthalocyanine derivatives were characterized by using proton nuclear magnetic resonance, mass spectrometry, ultraviolet–visible spectroscopy, and Fourier transform infrared spectroscopy. The HOMO–LUMO energies were computed using density functional theory. The HOMO–LUMO energy difference is 2.28 eV. The calculated results were consistent with the experimental data. In addition, aggregation behaviors and general trends for photophysical properties of these phthalocyanine derivatives were studied in tetrahydrofuran. The emission intensities of these phthalocyanine derivatives were strongly quenched by 1,4-benzoquinone in tetrahydrofuran.


Author(s):  
Muhamad Fikri Zaini ◽  
Ibrahim Abdul Razak ◽  
Wan Mohd Khairul ◽  
Suhana Arshad

The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, molecules are linked into inversion dimers with an R 2 2(10) graph-set motif via pairs of C—H...O hydrogen bonds. The intermolecular interactions were analysed and quantified by Hirshfeld surface analysis. The molecular structure was optimized and a small HOMO–LUMO energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6–311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV–vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996 (16):0.8004 (16).


2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Xue-Feng Ren ◽  
Jun Zhang ◽  
Guo-Jun Kang

To design efficient organic sensitizer, a series of D-π-A indoline dyes with different donor parts have been investigated by density functional theory (DFT) and time-dependent DFT (TD-DFT) approach. The molecular geometries, frontier molecular orbitals, and absorption spectra of these dyes have been systematically investigated to provide comprehensive understanding of the structure-property relationships. Compared with D149, our designed dyes have proper HOMO and LUMO energy level, narrowed HOMO-LUMO energy gap, and broadened absorption band by introducing the N(CH3)2and N(phenyl)2groups at the donor part. Furthermore, the dimeric dyes and dye-(TiO2)6systems have been optimized by DFT method to simulate the intermolecular interactions, as well as interaction between the dyes dimmers and semiconductor interface, respectively. Through the analyses of absorption energies (Eads), energy levels of the HOMO and LUMO, light harvesting efficiency (LHE), and the driving force of electrons injections (ΔGinject), it is found that the designed dyes should have improved optical properties by importing the N(CH3)2group. This work is hoped to provide a theoretical guiding role in design of new dyes for dye-sensitized solar cells.


2019 ◽  
Vol 3 (2) ◽  
pp. 95
Author(s):  
Fitra Perdana ◽  
Karna Wijaya ◽  
Ria Armunanto

AbstrakStudi secara teoritis telah dilakukan untuk mempelajari interaksi senyawa turunan kalkon hidroksi (CH) sebagai sensor kimia dengan anion F-, Cl-, Br-, CN-, CH3COO-, dan NO3-. Penelitian ini bertujuan untuk memodelkan struktur molekul senyawa turunan kalkon hidroksi (CH) dan sifat sensornya serta model interaksinya dengan anion dengan metode DFT. Hasil optimasi geometri menunjukkan terjadinya pemanjangan ikatan O-H sebesar 0,63-0,85 Å dengan adanya anion F-, CN-, and CH3COO-. Hal ini mengindikasikan terjadinya deprotonasi sensor kalkon hidroksi (CH) oleh anion. Sedangkan interaksi sensor kalkon hidroksi (CH) dengan anion Cl-, Br-, dan NO3- hanya berupa ikatan hidrogen dengan pemanjangan ikatan O-H sebesar 0,08-0,46 Å. Sensor kalkon hidroksi (CH) yang mengalami deprotonasi memiliki energi interaksi yang lebih besar yaitu -209,37 – -424,06 kJ/mol dibandingkan sensor yang hanya membentuk ikatan hidrogen yaitu -98,60 – -125,59 kJ/mol. Sensor yang mengalami deprotonasi mengakibatkan turunnya selisih energi HOMO-LUMO dari -3,94 – -4,06 eV menjadi -2,62 – -2,75 eV.Kata kunci: sensor kimia, kalkon hidroksi, anion, DFT  AbstractTheoretical study had been carried out to investigate interaction between hydroxy chalcone derivatives (CH) as chemosensors with F-, Cl-, Br-, CN-, CH3COO-, and NO3- anions. This study was aimed to design molecular structures of chemosensor hydroxy chalcone (CH) properties for the anions and their interaction models with DFT method. The result of geometry optimization showed 0,63-0,85 Å O-H bond elongation of the hydroxy chalcone was occured by F-, CN-, and CH3COO-. It was indicated deprotonation of sensor hydroxy chalcone (CH) by anions. Where as the interaction of the hydroxy chalcone (CH) with Cl-, Br-, and NO3- just formed an hydrogen bond with 0,08-0,46 Å O-H bond elongation. Deprotonized sensor hydroxy chalcone (CH) had more energy change of interaction -209,37– -424,06 kJ/mol than sensor which just formed the hydrogen bond -98,60 – -125,59 kJ/mol. Deprotonized sensor caused reduction of the difference of HOMO-LUMO energy from - 3,94 – -4,06 eV to -2,62 – -2,75 eV.Keywords: chemosensor, hydroxy chalcone, anion, DFT


2021 ◽  
Vol 8 (4) ◽  
pp. 20218415
Author(s):  
Igor L. Nikonov ◽  
Igor A. Khalymbadzha ◽  
Leila К. Sadieva ◽  
Maria I. Savchuk ◽  
Ekaterina S. Starnovskaya ◽  
...  

A rational synthetic approach to substituted naphtho[1,8-gh]quinolines using intramolecular cyclization in the presence of potassium in the series of (naphthalen-1-yl)isoquinolines is described. The photophysical properties of the obtained compounds were studied; in particular, fluorescence emission was detected in the range 454 - 482 nm with a quantum yield of up to 54%. We also calculated the HOMO-LUMO energies and optimized molecular structures for the resulting fluorophores. Based on the results of fluorescence titration, the Stern-Volmer constants (up to 21587 M-1) and the detection limits of nitroanalytes (up to 1.4 ppm) were calculated, confirming the possibility of their use as potential chemosensors for the visual detection of nitro-containing explosives.


Crystals ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1103
Author(s):  
Abdulrahman A. Alsimaree ◽  
Omar M. Alatawi ◽  
Paul G. Waddell ◽  
David P. Day ◽  
Nawaf I. Alsenani ◽  
...  

Two new pyrrolylquinoline-substituted heteroaromatic-containing compounds bearing a central boron bridge have been prepared by a short, high-yielding sequence consisting of Suzuki-coupling of 8-bromoquinoline and N-Boc 2-pyrroleboronic acid, thermolytic tert-butyloxycarbonyl deprotection, and subsequent boron chelation (either using boron trifluoride or triphenylborane). Both derivatives display longer wavelength absorption maxima (λabsmax) than a previously reported indolopyridine-BPh2 analogue, in agreement with the smaller HOMO-LUMO energy gap predicted by DFT quantum chemical calculations. Both of the pyrrolylquinoline-boron chelates display weak emission (quantum yields 0.3–0.9%) and the BPh2 complex displays a very broad, long-wavelength emission (λemmax = 715 nm, MeCN), which may be due to dimer emission and results in a large pseudo-Stokes’ shift (7753 cm−1) for this compound.


2020 ◽  
Vol 17 ◽  
Author(s):  
Ahmed Nuri Kursunlu ◽  
Elif Bastug ◽  
Ersin Guler

Background: Chemosensor compounds are useful for sensitive selective detection of cations and anions with fluorophore groups in an attempt to develop the effective selectivity of the sensors. Although familiar fluorescent sensors utilizing inter-molecular interactions with the cations and anions, an extraordinary endeavor was executed the preparation of fluorescent-based sensor compounds. 4,4-difluoro-4- bora-3a,4a-diaza-s-indacene (Bodipy) and its derivatives were firstly used as an agent in the imaging of biomolecules due to their interesting structures, complexation, and fluorogenic properties. Among the fluorescent chemosensors used for cations and anions, Bodipy-based probes stand out owing to the excellent properties such as sharp emission profile, high stability, etc. In this review, we emphasize the Bodipy-based chemosensor compounds, which have been used to image cations and anions in living cells, because of as well as the biocompatibility and spectroscopic properties. Methods: Research and online content related to chemosensor online activity is reviewed. The advances, sensing mechanisms and design strategies of the fluorophore exploiting selective detection of some cation and anions with Bodipy-based chemosensors are explained. It could be claimed that the using of Bodipy-based chemosensors is very important for cations and anions in bio-imaging applications. Results: Molecular sensors or chemosensors are molecules that show a change can be detected when affected by the analyte. They are capable of producing a measurable signal when they are selective for a particular molecule. Molecular and ion recognition that it is important in biological systems such as enzymes, genes, environment, and chemical fields. Due to the toxic properties of many heavy metal ions, it is of great importance to identify these metals due to their harmful effects on living metabolism and the pollution they create in the environment. This process can be performed with analytical methods based on atomic absorption and emission. The fluorescence methods among chemosensor systems have many advantages such as sensitivity, selectivity, low price, simplicity of using the instrument and direct determination in solutions. The fluorescence studies can be applied at nanomolar concentrations. Conclusion: During a few decades, a lot of Bodipy-based chemosensors for the detection of cations & anions have been investigated in bio-imaging applications. For the Bodipy-based fluorescent chemosensors, the Bodipy derivatives were prepared by different ligand groups for the illumination of the photophysical and photochemical properties. The synthesized Bodipy-based chemosensors have remarkable photophysical properties, such as a high quantum yield, strong molar absorption coefficient etc. Moreover, these chemosensors were successfully implemented on living organisms for the detection of analytes.


Author(s):  
Jihyeon Kim ◽  
Heechan Kim ◽  
Sechan Lee ◽  
Giyun Kwon ◽  
Taewon Kang ◽  
...  

A new bipolar-type redox-active organic material with a wide HOMO–LUMO energy gap is designed though the ‘p–n fusion’ strategy.


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