Synthesis, theoretical characterisation and spectra of thiophene–fluorene π-conjugated derivatives

Lukeš, Vladimı́r; Végh, Dániel; Hrdlovič, Pavol; Štefko, Martin; Matuszná, Katarína; Laurinc, Viliam

doi:10.1016/j.synthmet.2004.09.016

Cited by 15 publications

(5 citation statements)

References 22 publications

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“…However, the difference can be described by the molecular nodal patterns, because the excitation is mainly from HOMO to LUMO. Comparing Figure 9 with Figure 5 (HOMO and LUMO of torsional angle 08 are considered), the HOMO has nodes across r(4,5), r(1,2), r(12,11), r(8,9), r(6,7), r (15,16), and r(10,14) bonds in both FEDOT and FTSO2, but the LUMO is bonding in these regions. Therefore, the contraction of these bonds occurs.…”

Section: Excited-state Structure Of Fedot and Ftso2 Monomers And Emismentioning

confidence: 98%

Investigation of excited‐state properties of fluorene–thiophene oligomers by the SAC‐CI theoretical approach

Poolmee

Hannongbua

2010

J Comput Chem

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Excited states of fluorene-ethylenedioxythiophene (FEDOT) and fluorene-S,S-dioxide-thiophene (FTSO2) monomers and dimers were studied by the symmetry-adapted cluster (SAC)-configuration interaction (CI) method. The absorption and emission peaks observed in the experimental spectra were theoretically assigned. The first three excited states of the optimized conformers, and the conformers of several torsional angles, were computed by SAC-CI/D95(d). Accurate absorption spectra were simulated by taking the thermal average for the conformers of torsional angles from 0 degrees to 90 degrees. The conformers of torsional angles 0 degrees, 15 degrees, and 30 degrees mainly contributed to the absorption spectra. The full width at half-maximum of the FEDOT absorption band is 0.60 eV (4839 cm(-1)), which agrees very well with the experimental value of 0.61 eV (4900 cm(-1)). The maximum absorption wavelength is located at 303 nm, which is close to those of the experimental band (327 nm). The calculated absorption spectrum of FTSO2 showed two bands in the range of 225-450 nm. This agrees very well with the available experimental spectrum of a polymer of FTSO2, where two bands are detected. The excited-state geometries were investigated by CIS/6-31G(d). These showed a quinoid-type structure which exhibited a shortening of the inter-ring distance (0.06 A for FEDOT and 0.04 A for FTSO2). The calculated emission energy of FEDOT is 3.43 eV, which agrees very well with the available experimental data (3.46 eV). The fwhm(E) is about 0.49 eV (3952 cm(-1)), while the experimental fwhm is 0.43 eV (3500 cm(-1)). For FTSO2, two bands were also found in the emission spectrum.

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Section: Excited-state Structure Of Fedot and Ftso2 Monomers And Emismentioning

confidence: 98%

Investigation of excited‐state properties of fluorene–thiophene oligomers by the SAC‐CI theoretical approach

Poolmee

Hannongbua

2010

J Comput Chem

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“…The dichloromethane solution fluorescent spectra for compound 4g at room temperature reveal an emission peak at 522/498 nm (the exciting radiation set at 357/410 nm) as shown in Figure 2. The emission band may be attributed to the π–π* transition of the pyridine ring [17, 18].…”

Section: Luminescent Propertiesmentioning

confidence: 99%

Synthesis of 10‐amino‐9‐aryl‐2,3,4,5,6,7,9,10‐octahydroacridine‐1,8‐dione derivatives

Han

Cui

Chen

et al. 2011

Journal of Heterocyclic Chem

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A series of novel 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione derivatives 4 were synthesized by hydrazine or phenylhydrazine and 9-aryl-1,8-dioxo-2,3,4,5,6,7,9-heptahydroxanthene derivatives 3, which were prepared by 5-substituted-1,3-cyclohexanedione 1 and aromatic aldehydes 2 in the presence of concentrated H 2 SO 4 as a catalyst in water. The structures of all compounds were characterized by IR, MS, 1 H-NMR, and elemental analysis, and the title compounds possess good fluorescence properties.

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“…Fluorene-containing compounds have unique chemical behaviours and physical properties due to the unusual geometric structure of fluorene [1]. Fluorene and its derivatives are important materials that are used in organic synthesis, the pharmaceutical and synthetic resin industries, and conductivity research [2][3][4]. Acetylamino-, diacetylamino-, amino-and nitro-substituted fluorene compounds increase the biological effects [5,6] of an inhibitor of oncogenic tyrosine kinase [7], antimicrobial agents [8] and potent frameshift-type mutagens [9].…”

Section: Introductionmentioning

confidence: 99%

In vitro inhibition of purified human carbonic anhydrase I and II by novel fluorene derivatives

Demirhan

Arslan

Kaya

et al. 2014

Maced. J. Chem. Chem. Eng.

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In this study, 9-benzylidene-9H-fluorene-substituted urea (5a-p) and thiourea derivatives (5q-v) were synthesized and their inhibitory effects on the activity of human carbonic anhydrase (hCA) I and II were evaluated. hCA I and II were purified from human erythrocytes using a Sepharose 4B-L-tyrosinesulphanilamide affinity column. All the synthesized compounds inhibited the activity of the hCA I and II isoenzymes. Among the synthesized compounds, 5f was found to be the most active (IC 50 = 21.4 μM) for inhibition of hCA I and 5s was the most active (IC 50 = 25.3 μM) for inhibition of hCA II. IN VITRO ИНХИБИЦИЈА НА ПРЕЧИСТЕНА ЧОВЕЧКА КАРБОНСКА АНХИДРАЗА I И II СО НОВИ ФЛУОРЕНСКИ ДЕРИВАТИВо оваа студија беа синтетизирани деривати на уреа (5a-p) и тиоуреа (5q-v) добиени со супституција на 9-безилиден-9H-флуорен и беше проценет нивниот инхибиторен ефект врз човечка карбонска анхидраза (hCA) I и II. HCA I и II беа пречистени од човечки еритроцити со употреба на афинитетната колона Sepharose 4B-L-тирозин-сулфаниламид. Сите синтетизирани соединенија ја инхибираа активноста на изоензимите на hCA I и II. Од синтетизираните соединенија, 5f се покажа најактивно (IC 50 = 21,4 μM) за инхибиција на hCA I, додека 5s беше најактивно (IC 50 = 25,3 μM) за инхибиција на hCA II.Клучни зборови: 9-безилиден-9H-флуорен; уреа; тиоуреа; карбонска анхидраза; инхибиција

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Synthesis, theoretical characterisation and spectra of thiophene–fluorene π-conjugated derivatives

Cited by 15 publications

References 22 publications

Investigation of excited‐state properties of fluorene–thiophene oligomers by the SAC‐CI theoretical approach

Investigation of excited‐state properties of fluorene–thiophene oligomers by the SAC‐CI theoretical approach

Synthesis of 10‐amino‐9‐aryl‐2,3,4,5,6,7,9,10‐octahydroacridine‐1,8‐dione derivatives

In vitro inhibition of purified human carbonic anhydrase I and II by novel fluorene derivatives

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