262291-69-0Relevant academic research and scientific papers
Synthesis and characterization of organic dyes bearing new electron-withdrawing group for dye-sensitized solar cells
Salimi Beni,Zarandi,Madram,Bayat,Najafi Chermahini,Ghahary
, p. 504 - 511 (2015)
Three new carbazole-based dyes (DB-CH, DTB-CH, DT-CH) have been synthesized. The dye structures were built from an aliphatic hexyl which served as an electron donor and barbituric acid, thiobarbituric acid and thiazolidine-2,4-dione moieties which served as acceptors. The photophysical and electrochemical properties of the dyes were investigated by UV spectroscopy and cyclic voltammetry (CV). The barbituric acid, thiobarbituric acid and thiazolidine-2,4-dione derivatives were found to affect both the molar extinction coefficients and λmax which was likely due to the extension of the π-conjugation structures of the dyes. In the best case, conversion efficiencies up to 2.16% under full sunlight irradiation were obtained for the DSSCs which incorporated these new dyes. Our study indicated that the inclusion of thiazolidine-2,4-dione as an electron acceptor in the dye structure can lead to an improvement in its photovoltaic performance.
Design, self-assembly, and photophysical properties of pentameric metallomacrocycles: [M5(N-hexyl[1,2-bis(2,2′:6′,2″- terpyridin-4-yl)]carbazole)5][M = Fe(II), Ru(II), and Zn(II)]
Hwang, Seok-Ho,Wang, Pingshan,Moorefield, Charles N.,Godinez, Luis A.,Manriquez, Juan,Bustos, Erika,Newkome, George R.
, p. 4672 - 4674 (2005)
A novel family of metallopentacycles was constructed by the facile self-assembly of a bis(terpyridine)-carbazole monomer utilizing terpyridine-metal(II)-terpyridine connectivity; its photophysical properties were investigated. The Royal Society of Chemistry 2005.
A new carbazole-based helically chiral architecture: Synthesis and physical properties
Ben Braiek, Mourad,Aloui, Faouzi,Ben Hassine, Béchir
, p. 2763 - 2766 (2016)
A short and efficient synthesis leading to a new helically chiral heptacyclic system, containing a carbazole unit, was achieved via a Knoevenagel condensation-photocyclization strategy. The optical properties of the carbazole-based material were investigated by UV-vis absorption and photoluminescence spectroscopy and an emission in the visible region was observed. From the cyclic voltammetry analysis, the electrochemical band gap of the target organic material was estimated to be 2.38 eV indicating that it might be a good candidate for electron-injection hole-blocking layers in organic light-emitting diodes.
Luminescence feature of new 3,6-di(thiazolidin-5-one-2-yl)-carbazole derivative: synthesis, photophysical properties, density functional theory studies, and crystal shape effect
Bawazeer, Tahani M.,Althagafi, Ismail,Morad, Moataz,Munshi, Alaa M.,Bayazeed, Abrar A.,Alharbi, Arwa,El-Metwaly, Nashwa
, p. 904 - 913 (2021/02/01)
A new carbazole chromophore conjugated with substituted thiazolidine-4-one (CzPT) was synthesized by applying the Knoevenagel reaction between 3,6-diformyl-N-hexylcarbazole and ethyl 2-aceto-2-(5-oxo-3-phenylthiazolidin-2-ylidene)acetate. The chemical structure of the new derivative (CzPT) was elucidated by spectral studies. The CzPT absorption spectra in different solvents exhibited a red shift for λmax by increasing solvent polarity. Bands at 430–474 nm appeared and were attributed to intramolecular charge transfer with high π–π* characteristics. CzPT fluorescence spectra exhibited a red shift after increasing the solvent polarity. To understand the Stokes' shift ((Formula presented.) behaviour of the CzPT derivative referring to the polarity of solvents, Lippert–Mataga and linear solvation-energy relationship (LSER) models were employed in which the LSER exhibited respectable results compared with Lippert–Mataga (r2 = 0.9707). Moreover, time-dependent density functional theory absorption spectra in hexane and dimethylformamide showed that λmax had a major contribution in the highest occupied molecular orbital to lowest unoccupied molecular orbital transition in both solvents. In addition, the reduced uniformity of crystal features may lead to dislocation or anomalous arrangement of crystals with irregular spacing, which automatically enhances the optical properties of such crystals.
Effect of different acceptors on N-hexyl carbazole moiety for dye-sensitized solar cells: design, characterization, molecular structure, and DSSC fabrications
Abusaif, Moustafa S.,Abu-Saied,Fathy,El-Sherif, Ahmed A.,Kashyout,Selim, Mohamed R.,Ammar, Yousry A.
, p. 949 - 960 (2020/10/19)
Hexyl carbazole derivatives are one of the most prominent dye scaffolds in the dye-sensitized solar cells (DSSCs). New substituted carbazole dyes such as DRA-HC, DCA-HC, and DTC-HC were synthesized for DSSCs. These dyes are containing hexyl moiety as electron donor and rhodanine-3-acetic acid, cyanoacetic acid and tetracyanoethylene as an electron acceptor linked to carbazole moiety. The relation between dye structures, photophysical/electrochemical, molecular structure and DSSC manufacturing had been discussed. All structures showed more positive ground-state oxidation potential than I?/I?3 and more negative excited state oxidation potential than the conduction band edge of the semiconductor. The highest efficiency of the DSSCs was obtained in the case of DCA-HC dye (η = 1.41%, VOC = 708?mV, FF = 0.81, and JSC = 2.45?mA?cm?2 with 100?mW?cm?2) compared to other synthesized dyes.
Single and double branched organic dyes based on carbazole and red-absorbing cationic indolium for p-type dye-sensitized solar cells: A combined experimental and theoretical investigation
Bao, Le Quoc,Ho, Phuong,Chitumalla, Ramesh Kumar,Jang, Joonkyung,Thogiti, Suresh,Kim, Jae Hong
, p. 25 - 36 (2017/10/05)
A series of novel single and double branched carbazole-based red-absorbing cationic dyes without (CSI and CDI) and with (CST and CDT) a thiophene spacer have been synthesized for p-type dye-sensitized solar cells (p-DSSCs). The introduction of the red-absorbing cationic acceptor/thiophene spacer led to the broadening and bathochromic shift of the absorption maxima from an onset of 600 nm for CSI to 800 nm for CDT as well as improved molar absorptivity. The introduction of the double branching/thiophene spacer lowered the lowest unoccupied molecular orbital (LUMO) levels of CDI, CST, and CDT, making their potentials more positive than that of CSI. Among these, the double branched CDI exhibited the highest conversion efficiency of 0.112%. Furthermore, all of the dyes examined outperformed the standard C343 dye (0.062%), measured under similar fabrication conditions. Despite the decreased photovoltaic performance as a result of the introduction of the thiophene spacer, overall, the double branched dyes exhibited better interfacial charge transfer that led to higher JSC and VOC values compared to those of singly branched dyes. Electrochemical impedance spectroscopy analysis showed that double branched dyes have much lower charge transfer resistance and increased hole lifetime than single branched dyes. Density functional theory (DFT) and time-dependent DFT calculations were performed to theoretically characterize the optical and electrochemical properties of the synthesized dyes.
Synthesis of carbazole-based copolymers containing carbazole-thiazolo[5,4-: D] thiazole groups with different dopants and their fluorescence and electrical conductivity applications
Sathiyan, Govindasamy,Thangamuthu, Rangasamy,Sakthivel, Pachagounder
, p. 69196 - 69205 (2016/08/05)
To improve the electrical conductivity of poly(carbazole-thiazolo[5,4-d]thiazole) (p-CzTT), five different dopants, such as HCl, Fe(iii), Cu(ii), H3BO3, and I2, were introduced into its framework through protonation of a nitrogen atom or by complex formation. Carbazole-thiazolo[5,4-d]thiazole (CzTT) and poly(carbazole-thiazolo[5,4-d]thiazole) (p-CzTT) were synthesized by the reactions of carbazole aldehydes and dithiooxamide. The synthesized monomer and polymer were confirmed by FT-IR, UV-vis, 1H, 13C-NMR, and GPC studies. The doped polymers were examined by FT-IR spectroscopy, UV-visible absorption, fluorescence, thermogravimetric analysis (TGA), cyclic voltammetry (CV), and electrical conductivity. The optical band gap (Eoptg) of CzTT and p-CzTT were found to be 2.74 eV and 1.95 eV, respectively. The thermal stability of the polymer showed 5% weight loss at 358 °C. Based on CV analysis, the HOMO and LUMO energy levels and the electrochemical band gap (Ecvg) of p-CzTT were obtained as -5.86 eV, -3.19 eV, and 2.67 eV, respectively. The CzTT and p-CzTT exhibited fluorescence emission at 461 nm and 448 nm, respectively. Among the dopants introduced, Fe(iii)- and I2-doped polymer showed excellent electrical conductivities of 6.8 × 10-5 S cm-1 and 5.9 × 10-5 S cm-1, respectively.
Bi-anchoring organic sensitizers of type D-(π-A)2 comprising thiophene-2-acetonitrile as π-spacer and malonic acid as electron acceptor for dye sensitized solar cell applications
Reddy, Gachumale Saritha,Ramkumar, Sekar,Asiri, Abdullah M.,Anandan, Sambandam
, p. 531 - 539 (2015/03/31)
Two new bi-anchoring organic sensitizers of type D-(π-A)2 comprising the identical π-spacer (thiophene-2-acetonitrile) and electron acceptor (malonic acid) but different aryl amine as electron donors (diphenylamine and carbazole) were synthesized, characterized and fabricated metal free dye-sensitized solar cell devices. The intra molecular charge transfer property and electrochemical property of these dyes were investigated by molecular absorption, emission, cyclic voltammetric experiments and in addition, quantum chemical calculation studies were performed to provide sufficient driving force for the electron injection into the conduction band of TiO2 which leads to efficient charge collection. Among the fabricated devices, carbazole based device exhibits high current conversion efficiency (η = 4.7%) with a short circuit current density (JSC) 15.3 mA/cm2, an open circuit photo voltage (VOC) of 0.59 V and a fill factor of 0.44 under AM 1.5 illumination (85 mW/cm2) compared to diphenylamine based device.
Synthesis and characterization of new carbazole-based materials for optoelectronic applications
Bahy, Amira,Chemli, Mejed,Hassine, Béchir Ben
, p. 4026 - 4029 (2013/07/26)
New triazolo-carbazole derivatives were synthesized by copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. The chemical structures of these compounds were confirmed by NMR and FT-IR spectroscopic analysis. The optical properties of the triazolo-carbazoles were investigated by UV-visible absorption and photoluminescence spectroscopy; an emission in the ultraviolet region was observed. The energy levels of these organic materials were determined by cyclic voltammetry and showed a relatively high electronic affinity indicating that they might be good candidates for electron-injection hole-blocking layers in organic light-emitting diodes.
Synthesis of bianchored metal free organic dyes for dye sensitized solar cells
Ramkumar, Sekar,Anandan, Sambandam
, p. 397 - 404 (2013/04/24)
Two bianchored metal free organic dyes (Car-th-CN and Dpa-th-CN) were designed and synthesized for DSSC application, in which carbazole or diphenylamine moieties were used as the donor, cyano vinyl thiophene unit as the π-bridge and cyanoacrylic acid group as the electron acceptor. The structures of the synthesized dyes were confirmed by NMR, HR-Mass and elemental analysis. The optical, electrochemical, theoretical and photovoltaic properties of the synthesized dyes were investigated. Fabricated photovoltaic devices based on carbazole unit as a donor (Car-th-CN) showed a maximum current conversion efficiency of 4.04% under AM 1.5 illumination (85 mW cm-2) and monochromatic incident photon to current efficiency (IPCE) of 38.1%. The reason for the higher efficiency of Car-th-CN is due to the planar nature of carbazole moiety and hence increases the capability of adsorbed dye amount and electron lifetime in TiO2 surface.
