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1.
Ramírez MA Cuadro AM Alvarez-Builla J Castaño O Andrés JL Mendicuti F Clays K Asselberghs I Vaquero JJ 《Organic & biomolecular chemistry》2012,10(8):1659-1669
Heteroaromatic cations reacted with N-heteroarylacetylenes under Sonogashira conditions to allow easy access to potential single donor D-π-A(+) and V-shaped D-π-A(+)-π-D chromophores, where the acceptor moiety A is the π-deficient pyridinium cation and the donor moiety is represented by different π-excessive N-heterocycles. The β hyperpolarizabilities were measured using hyper-Rayleigh scattering experiments and the experimental data are supported by a theoretical analysis that combines a variety of computational procedures, including Density Functional Theory (DFT) and correlated Hartree-Fock-based methods (RCIS(D)). 相似文献
2.
Tanika Khanasa Narid Prachumrak Palita Kochapradist Supawadee Namuangruk Tinnagon Keawin Siriporn Jungsuttiwong Taweesak Sudyoadsuk Vinich Promarak 《Tetrahedron letters》2014
New D-π-A-π-A type organic dyes were synthesized and characterized as sensitizers for dye-sensitized solar cells (DSSCs). These dyes showed wide absorption spectra (300–625 nm) and high molar extinction coefficients (ε467 nm = 60,911 M−1 cm−1). As dye sensitizers in DSSC, the D-π-A-π-A dye having a cyanoacrylic acid as an acceptor gave the best cell performance with a short-circuit photocurrent density (Jsc) of 7.14 mA/cm2, an open-circuit voltage (Voc) of 0.62 V, and a fill factor (FF) of 0.72, corresponding to an overall conversion efficiency η of 3.19%. 相似文献
3.
A series of 4,4'-π-conjugated-2,2'-bipyridine chromophores (MS 1-8) were synthesized, and their photophysical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a π-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-π-A-A-π-D dyad archetype in which the A-A is the central 2,2'-bipyridine acceptor core that is electronically attached with the donor termini through π-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field. 相似文献
4.
Munusamy Anbarasan Ponnusamy Ammasi Arunkumar Shajahan Shanavas Ahamad Tansir Khan M. A. Majeed 《Structural chemistry》2021,32(6):2199-2207
Structural Chemistry - In this work, the newly designed phenothiazine-based organic dye (PT-BTBA, PT-EBTBA, and PT-EBTEBA) derivatives were screened and investigated for dye-sensitized solar cell... 相似文献
5.
Hassan A. El-Sayed Ahmed H. Moustafa Esraa A. Abd El-Salam 《Journal of heterocyclic chemistry》2020,57(7):2738-2747
Study the synthesis and fluorescent properties of a new series of D-π-A fluorescent dyes based on nicotinonitrile and azobenzene is the main objective for this work. Reduction with Zn/HCl, diazotization with HCl/NaNO2, and coupling using catalytic NaOH or AcONa are simple applied methods. Where, nicotinonitrile 3 was synthesized via reduction of nitro derivative 1 followed by diazotization with HCl/NaNO2 in acetic acid. The formed benzene diazonium chloride was coupled with several activated phenols, aniline, and α-CH acids to yield the respective azo dyes 4-11 in moderate to good yield. Dyes 11a-d subjected to intermolecular cyclization with hydrazine hydrate resulted in pyrazole dyes 12-15 in moderate yield. Dyes containing pyrazole moiety or electron-withdrawing groups at the sixth position of pyridine nucleus exhibit stronger blue-green emission (λfl.max = 503, 507, 500, 501, 502, 493, and 514 nm) than that of the rest of compounds. 相似文献
6.
Kim SH Gwon SY Bae JS Son YA 《Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy》2011,78(1):234-237
A new donor-π-acceptor (D-π-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)-malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by 1H NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with "on" and "off" states. 相似文献
7.
ZENG Juan ZHANG TengLong ZANG XuFeng KUANG DaiBin MEIER Herbert CAO DeRong 《中国科学:化学(英文版)》2013,56(4):505-513
Three novel triphenylamine-based D-A-π-A-featured dyes (Z1-Z3) have been designed, synthesized and characterized for use in dye-sensitized solar cells. Benzothiazole was incorporated as an additional acceptor, which greatly enhanced the molar extinction coefficient of the dyes. Various conjugated linkers, such as benzene, furan and thiophene, were also introduced to configure the novel D-A-π-A framework in order to prolong electron flow and active transportation. Among all dyes, Z2 containing a thiophene linker exhibited the maximum overall conversion efficiency (η) of 4.16% (Jsc = 9.27 mA cm-2 , Voc = 642 mV, FF = 0.70) under standard global AM 1.5 G solar condition. 相似文献
8.
Rui Yuan Longyan Zhang Lichuan Chen Haoli Zhang Pengfei Dou Xuanxuan Ren Wen Chen Hang Zhou Yu Wan Hui Wu 《Tetrahedron letters》2019,60(27):1803-1807
Available online A series of diphenylamine (DPA)-containing triarylamine-based D-D-π-A organic fluorescence dyes were designed under the guidance of theoretical calculations and then synthesized (cyanoacrylic acid, methylene malononitrile or isophorone served as the electron acceptor while ethylene served as the π-bridge). The results of theoretical calculations, electrochemical properties and optical properties tests indicated that the new dyes possessed high thermal stability, desirable HOMO levels and intramolecular charge transfer property. Some of them possessed high fluorescence quantum yields and performed very well as luminescent material as expected.. 相似文献
9.
《结构化学》2016,(9)
A novel D-π-A type α-cyanostilbenzene derivative,(Z)-2-(4-aminophenyl)-3-(4-bromophenyl)-acrylonitrile(ABAN), was designed and synthesized, by introducing an electrondonating amino group and a heavy atom. The structure of ABAN was confirmed by FT-IR, 1H NMR, 13 C NMR spectra and single-crystal X-ray diffraction analysis. The ABAN is of orthorhombic system, space group P212121, with a = 8.6100(14), b = 9.6923(16), c = 15.705(3) ?, Mr = 299.17, V = 1310.6(4) ?3, Z = 4, Dc = 1.516 g/cm-3, μ = 3.119 mm-1, F(000) = 600, Rint = 0.038, R(I 2σ(I)) = 0.0276, w R(I 2σ(I)) = 0.0628, R(all data) = 0.0324, wR(all data) = 0.0646, completeness to theta = 25.00 was 99.8% and GOOF = 1.04. In the crystal structure, ABAN molecules were linked with each other through intermolecular C–H···π interactions and N–H···N hydrogen bonds, by which the 1D chain, 2D plane and 3D stacking structures were constructed. The photophysical properties and calculation results confirmed that ABAN possessed an intramolecular charge transfer(ICT) process. ABAN could be applied into the optoelectronic material field due to good solvent-tuned photophysical properties and highly thermal stability. 相似文献
10.
Izabela Janowska Keitaro Nakatani Marcin Walak 《Journal of organometallic chemistry》2006,691(3):323-330
Second-order nonlinear optical chromophores incorporating the ferrocenyl group as an electron donor and 3-dicyanomethylidene-1-indanone and 1,3-bis(dicyanomethylidene)indane acceptor groups, connected by a conjugated polyenic bridge of varied length (2[n] and 3[n], respectively) have been synthesized. The electronic absorption spectra of these compounds display in the visible region bands attributable to π-π* and metal-to ligand charge transfer (MLCT) transitions. The energies of these transitions are close to those reported earlier for ferrocenyl D-π-A chromophores with the strongest acceptor groups, e.g., with the 3-dicyanomethylidene-2,3-dihydrobenzothiophene-1,1-dioxide group (1[n]) [V. Alain, M. Blanchard-Desce, C.-T. Chen, S.R. Marder, A. Fort, M. Barzoukas, Synt. Met. 81 (1996) 133]. The solid-state structure of 2[3], determined by X-ray diffraction shows a significant reduction of the bond length alternation (BLA), 0.05 Å, suggesting high first hyperpolarizability. However, a centrosymmetrical packing of molecules of this compound in the crystal excludes its second harmonic generation ability. The μβ values of 2[n] and 3[n], determined by the EFISH technique at 1907 nm are high and increase with the increasing length of the conjugated π-bridge. The highest value of μβ (8720 × 10−48 esu) was determined for 3[4], which is close to that reported for 1[4] (11 200 × 10−48 esu), the highest value found for a ferrocenyl D-π-A chromophore until now. 相似文献
11.
Antonio Garrido Montalban Antonio J. HerreraJes Johannsen Andrew J.P. WhiteDavid J. Williams 《Tetrahedron》2014
Mono- and tri-topic ligands, based on dipyrromethenes and the 1,10-phenanthroline nucleus, as well as BF2 complexes derived thereof are described. While BODIPY 12 has been X-ray crystallographically characterized, the structural features of the free ligands 9 and 10 may render them useful as precursors for the elaboration of novel supramolecular architectures. 相似文献
12.
Donor–acceptor, perylenediimide–ferrocene conjugates have been synthesized by Suzuki, and Sonogashira coupling reactions. The photophysical and electrochemical properties of these conjugates are discussed. It has been shown that fluorescence as well as the electron affinity of the perylenediimide can be tuned by attaching the appropriate ferrocenyl derivatives. 相似文献
13.
Two Schiff bases of D-p-D type (L1 and L2) have been successfully synthesized by the reaction of 3,3′-dimethylnapthide and 3,3′,5,5′-tetramethylbenzidine with 4-(dimethylamino)cinnamic aldehyde. The ligands L1 and L2 have been characterized by IR, UV-visible, 1H NMR and fluorescence spectra, as well as, TGA-DSC-DTG, elemental analyses and mass spectra. 相似文献
14.
Weber L Eickhoff D Marder TB Fox MA Low PJ Dwyer AD Tozer DJ Schwedler S Brockhinke A Stammler HG Neumann B 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(5):1369-1382
Four linear π-conjugated systems with 1,3-diethyl-1,3,2-benzodiazaborolyl [C(6)H(4)(NEt)(2)B] as a π-donor at one end and dimesitylboryl (BMes(2)) as a π-acceptor at the other end were synthesized. These unusual push-pull systems contain phenylene (-1,4-C(6)H(4)-; 1), biphenylene (-4,4'-(1,1'-C(6)H(4))(2)-; 2), thiophene (-2,5-C(4)H(2)S-; 3), and dithiophene (-5,5'-(2,2'-C(4)H(2)S)(2)-; 4) as π-conjugated bridges and different types of three-coordinate boron moieties serving as both π-donor and π-acceptor. Molecular structures of 2, 3, and 4 were determined by single-crystal X-ray diffraction. Photophysical studies on these systems reveal blue-green fluorescence in all compounds. The Stokes shifts for 1, 2, and 3 are notably large at 7820-9760 cm(-1) in THF and 5430-6210 cm(-1) in cyclohexane, whereas the Stokes shift for 4 is significantly smaller at 5510 cm(-1) in THF and 2450 cm(-1) in cyclohexane. Calculations on model systems 1'-4' show the HOMO to be mainly diazaborolyl in character and the LUMO to be dominated by the empty p orbital at the boron atom of the BMes(2) group. However, there are considerable dithiophene bridge contributions to both orbitals in 4'. From the experimental data and MO calculations, the π-electron-donating strength of the 1,3-diethyl-1,3,2-benzodiazaborolyl group was found to lie between that of methoxy and dimethylamino groups. TD-DFT calculations on 1'-4', using B3LYP and CAM-B3LYP functionals, provide insight into the absorption and emission processes. B3LYP predicts that both the absorption and emission processes have strong charge-transfer character. CAM-B3LYP which, unlike B3LYP, contains the physics necessary to describe charge-transfer excitations, predicts only a limited amount of charge transfer upon absorption, but somewhat more upon emission. The excited-state (S(1)) geometries show the borolyl group to be significantly altered compared to the ground-state (S(0)) geometries. This borolyl group reorganization in the excited state is believed to be responsible for the large Stokes shifts in organic systems containing benzodiazaborolyl groups in these and related compounds. 相似文献
15.
《Journal of Coordination Chemistry》2012,65(15):1309-1319
Three Keggin-type polyoxometalates functionalized by amino acids, (C5H13N2O2)2(H3O)PMo12O40·8H2O 1, (C5H14N2O2)2SiMo12O40·12H2O 2 and (C5H14N2O2)2GeMo12O40·12H2O 3, were synthesized and characterized by elemental analysis, IR and 1H?NMR spectra and single-crystal X-ray diffraction. The X-ray crystallographic study showed that the structures of the three compounds involved N–H···O and O–H···O hydrogen bonds among the protonated ornithine cations, water molecules and the heteropolyanion cluster, and thus represent a model interaction between polyoxometalates and proteins. These complexes display inhibitory actions to the human cancer cells Hela and PC-3?m in vitro. 相似文献
16.
An electron donor-π-bridge-electron acceptor(D-π-A) optical functional organic compound comprising a triphenylamine moiety as the electron donor and pyridine moiety as the electron acceptor was synthesized. The structure of the compound was solved by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, with a = 9.753(5), b = 8.815(5), c = 25.554(5) ?, β = 96.315(5)°, V = 2184(2) ?~3, Z = 2, D_c = 1.136 g/m~3, F(000) = 792, Μr = 746.92, μ = 0.069 mm~(-1), the final R = 0.0658 and wR = 0.1730 for 6790 observed reflections with I 2(I). Study of nonlinear optical properties shows that the compound exhibits excellent two-photon excited fluorescence with the two-photon absorption cross-section value of 116 GM. The structure-property relationship was researched in detail through X-ray crystallography and quantum chemical calculation. Result of living cell imaging experiment shows its potential in fluorescence microscopy bioimaging. 相似文献
17.
Jing Yang Xiaofang Wang Hui Wen Fang Qin Guang Zhong Yang 《中国化学快报》2007,18(7):814-816
A series of phenylbenzamidine analogs were synthesized and tested for their biological activities of inhibiting the reuptake of 5- HT. All of them were new compounds, and their structures were confirmed by 1HNMR, MS and XRD. 相似文献
18.
Morad Moataz Habeebullah Turki M. Althagafi Ismail Asghar Basim H. Bayazeed Abrar A. Bawazeer Tahani M. Al-Solimy Amerah M. El-Metwaly Nashwa 《Research on Chemical Intermediates》2020,46(10):4543-4562
Research on Chemical Intermediates - Novel copper complexes were prepared from acetanilide derivatives and deliberately characterized. The molar ratio obtained was 1:1 through neutral bi-dentate... 相似文献
19.
Lukasz Szymanski Praveen Surolia Owen Byrne K. Ravindranathan Thampi Cosima Stubenrauch 《Colloid and polymer science》2013,291(4):805-815
The synthesis of porous “sponge-like” TiO2 via a polymer gel coating technique is presented. The experimental procedure involves the preparation of a gelled polymerizable microemulsion. The polymerization of the latter leads to porous poly-N-isopropylacrylamide which forms a hydrogel in the presence of water. Via solvent exchange, a suitable TiO2 precursor is infiltrated into this structure after which its in situ hydrolysis is triggered to form porous amorphous TiO2. The subsequent calcination step allows the removal of the polymer template and the transformation of amorphous TiO2 into porous, crystalline anatase with domain sizes ranging from 200 to 250 nm. As a means of verification and proof of concept, this material is tested as light-scattering layer in dye-sensitized solar cells (DSSC), and it is found that the resulting solar cell performance is comparable to commercially available TiO2. However, an increased tendency to form rutile during DSSC fabrication was noticed when compared to commercial TiO2. As there is a large potential for optimizing the synthesis, the proposed procedure is a promising route towards porous TiO2 that performs significantly better as scattering layer in light-harvesting and optical devices. 相似文献
20.
《Arabian Journal of Chemistry》2022,15(3):103651
The present study comprised of the synthesis of dicyanoaniline derivatives of pyridine, thiophene, furan, and substituted phenyl 1–29. All synthetic derivatives were evaluated for their potential to inhibit α-amylase and α-glucosidase enzymes. The synthesized compounds are classified into three categories A, B, and C based on variable substituents at R1 and R2, and the structure–activity relationship was discussed accordingly. Amongst twenty-nine derivatives, 1–29, five compounds 2, 9, 18, 23, and 24 displayed excellent inhibition against α-amylase and α-glucosidase enzymes with the IC50 values ranging between 20.33 ± 0.02–25.50 ± 0.06 µM and 21.01 ± 0.12–27.75 ± 0.17 µM, respectively, while other compounds showed moderate to weak inhibition against both enzymes. Acarbose was used as the positive control in this study. The enzyme kinetic studies showed non-competitive and un-competitive types of inhibition mechanism against α-amylase and α-glucosidase enzymes, respectively. In silico studies have demonstrated the involvement of these molecules in numerous binding interactions within the active site of the enzyme. 相似文献