110662-13-0Relevant academic research and scientific papers
Heteroleptic copper(I) sensitizers with one versus two hole-transporting units in functionalized 2,9-dimethyl-1,10-phenanthroline ancillary ligands
Fürer, Sebastian O.,Bozic-Weber, Biljana,Neuburger, Markus,Constable, Edwin C.,Housecroft, Catherine E.
, p. 69430 - 69440 (2015)
A series of homoleptic [Cu(L)2][PF6] complexes in which L is a 2,9-dimethyl-1,10-phenanthroline fused at the 5,6-positions with a 2′-functionalized imidazole (ligands 1-4), or substituted at the 4,7-positions with electron-donating 4-(diphenylamino)phenyl groups (ligand 5) is described; the imidazole 2′-functionality in 1 is 4-bromophenyl, in 2 is 4-(diphenylamino)phenyl, in 3 is 4-(bis(4-n-butoxy)phenylamino)phenyl, and in 4 is 4-(carbazol-9-yl)phenyl. The copper complexes were characterized by mass spectrometry, NMR and absorption spectroscopies and cyclic voltammetry; the single crystal structure of ligand 4 has been determined. Compared to the solution absorption spectra of [Cu(1)2][PF6], [Cu(2)2][PF6], [Cu(3)2][PF6] and [Cu(4)2][PF6], that of [Cu(5)2][PF6] shows increased absorbance at wavelengths >375 nm. An on-surface strategy was used to assemble heteroleptic [Cu(6)(L)]+ dyes on TiO2 electrodes where 6 is ((6,6′-dimethyl-[2,2′-bipyridine]-4,4′-diyl)bis(4,1-phenylene))bis(phosphonic acid); solid-state absorption spectra confirmed enhanced light-harvesting between 375 and 600 nm for [Cu(6)(5)]+ with respect to [Cu(6)(1)]+, [Cu(6)(2)]+, [Cu(6)(3)]+ and [Cu(6)(4)]+. Comparison of the performances of dye-sensitized solar cells (DSCs) containing [Cu(6)(2)]+, [Cu(6)(3)]+ and [Cu(6)(4)]+ with those with [Cu(6)(1)]+ indicate only a marginal influence of the diphenylamine or carbazole hole-transporting domains in 5,6-substituted phenanthroline dyes. The introduction of the 4-(diphenylamino)phenyl hole-transporting units in the 4- and 7-positions of the phen unit in 5 proves to be beneficial, with DSCs containing [Cu(6)(5)]+ performing better than those with the other four dyes; duplicate DSCs were tested for each dye to validate the results. While the values of the maximum external quantum efficiencies (EQEmax) for [Cu(6)(1)]+ and [Cu(6)(4)]+ are greater than for [Cu(6)(5)]+, the extension of the EQE spectrum for [Cu(6)(5)]+ to longer wavelengths results in higher short-circuit current densities (JSC) compared to DSCs with [Cu(6)(1)]+, [Cu(6)(2)]+, [Cu(6)(3)]+ and [Cu(6)(4)]+.
9,9′-bifluorenylidene derivatives as novel hole-transporting materials for potential photovoltaic applications
Kula, Slawomir,Paj?k, Agnieszka,Szlapa-Kula, Agata,Mieszczanin, Angelika,Gnida, Pawe?,Lipiński, Marek,Schab-Balcerzak, Ewa
, (2020)
Novel 9,9′-bifluorenylidene derivatives were designed to study the effect of alkyl chain length on selected physical properties. The structure of the synthesized compounds was confirmed by using NMR spectroscopy (1H, 13C, H–H COSY, H–C HMQC, H–C HMBC) and elemental analysis. They showed high thermal stability and undergo decomposition in the range of 388–400 °C. As was revealed by DSC investigations, they can be converted from crystalline to amorphous materials with relatively high glass transition temperature. The replacement of the alkyl chains from ethyl to butyl resulted in a significant negative impact on melting and glass transition temperatures. The synthesized derivatives undergo reversible electrochemical oxidation and reduction and showed a very low energy band gap (1.47 and 1.79 eV). They intensively absorb the light up 550 nm and also exhibited a week absorption band in the range of 550–750 nm. Their hole transporting ability was tested in perovskite solar cells. Additionally, the effect of the doping concentration of Li+ on photovoltaic device performance for these compounds was investigated. It should be stressed found that 9,9′-bifluorenylidene derivative substituted with ethyl units applied as hole transporting materials in perovskite solar cells demonstrated the highest device efficiency of 7.33% higher than of the spiro-OMeTAD utilized for preparation of the reference cell (4.40%).
Organic hole transport material and preparation method and application thereof
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, (2019/07/01)
The invention provides an organic hole transport material and a preparation method and application thereof. The structural general formula of the organic hole transport material is shown in the specification, and in the formula, R is ethyl, propyl, isopropyl or butyl. The preparation method is simple and easy to implement, the structure is definite, and the prepared organic hole transport materialhas high photoelectric conversion efficiency and can be applied to perovskite solar cells.
Bis[bis-(4-alkoxyphenyl)amino] derivatives of dithienylethene, bithiophene, dithienothiophene and dithienopyrrole: Palladium-catalysed synthesis and highly delocalised radical cations
Odom, Susan A.,Lancaster, Kelly,Beverina, Luca,Lefler, Kelly M.,Thompson, Natalie J.,Coropceanu, Veaceslav,Bredas, Jean-Luc,Marder, Seth R.,Barlow, Stephen
, p. 9637 - 9646 (2008/09/21)
Five diamines with thiophene-based bridges-(E)-1,2-bis-{5-[bis(4- butoxyphenyl)amino]-2-thienyljethylene (1), 5,5′-bis[bis(4-methoxyphenyl) amino]-2,2′-bithiophene (2), 2,6-bis[bis(4-butoxyphenyl)amino]dithieno[3, 2-b:2′,3′-d]thiophene (3), N-(4-tert-butylphenyl)-2,6-bis[bis(4- methoxyphenyl)amino]dithieno[3,2-b:2′,3′-d]pyrrole (4a) and N-tert-butyl-2,6-bis[bis(4-methoxyphenyl)amino]dithieno[3,2-b:2′, 3′-d]pyrrole (4b)-have been synthesised. The syntheses make use of the palladium(0)-catalysed coupling of brominated thiophene species with diarylamines, in some cases accelerated by microwave irradiation. The molecules all undergo facile oxidation, 4b being the most readily oxidised at about -0.4 V versus ferrocenium/ferrocene, and solutions of the corresponding radical cations were generated by addition of tris(4-bromophenyl)aminium hexachloroantimonate to the neutral species. The near-IR spectra of the radical cations show absorptions characteristic of symmetrical delocalised species (that is, class III mixed-valence species); analysis of these absorptions in the framework of Hush theory indicates strong coupling between the two amine redox centres, stronger than that observed in species with phenylenebased bridging groups of comparable length. The strong coupling can be attributed to high-lying orbitais of the thiophene-based bridging units. ESR spectroscopy indicates that the coupling constant to the amino nitrogen atoms is somewhat reduced relative to that in a stilbene-bridged analogue. The neutral species and the corresponding radical cations have been studied with the aid of density functional theory and time-dependent density functional theory. The DFT-calculated ESR parameters are in good agreement with experiment, while calculated spin densities suggest increased bridge character to the oxidation in these species relative to that in comparable species with phenylene-based bridges.
