36809-26-4Relevant articles and documents
Comparison of two strategies to improve organic ternary memory performance: 3-Hexylthiophene linkage and fluorine substitution
Bao, Qing,Li, Hua,Li, Yang,He, Jinghui,Xu, Qingfeng,Li, Najun,Chen, Dongyun,Wang, Lihua,Lu, Jianmei
, p. 306 - 313 (2016)
In this paper, two acceptor-donor-acceptor (A-D-A) type organic small molecules, 4,4'-(5,5'-(benzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(3-hexylthiophene-5,2-diyl))bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2TBT) and 4,4'-(5,6-difluorobenzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2BTF2), were synthesized and fabricated into resistive random access memory devices. Compared with our previously reported molecule NTPA2BT, NTPA2TBT has 3-hexylthiophene linkages bridging its donor and acceptor, while there are two additional fluorine atoms in the benzothiadiazole moiety for NTPA2BTF2. Both the fabricated memory devices based on these two new molecules perform nonvolatile ternary memory characteristics with lower threshold voltages, higher reproducibility and better stability. The addition of 3-hexylthiophene bridges significantly promotes the planarity of the conjugation backbone and facilitates the molecular stacking, while the substitution hydrogen by fluorine improves the intermolecular interaction, and thus also induces an ordered molecular stacking. The insertion of 3-hexylthiophene bridges or fluorine atoms could be an effective strategy of tailoring organic molecules to improve data storage performance with lower power consumption.
13C NMR Study of ortho-, meta- and para-Substituted Phenylhiphenylamines: Substituent Effect Correlations
Grimley, Eugene,Collum, David H.,Alley, Earl G.,Layton, Bobby
, p. 296 - 302 (1981)
The 13C chemical shifts of 11 substituted triphenylamines have been determined and the assignment of these resonances made using intensities, 1H and 19F couplings and predictions from bond additivity relationships. 13C chemical shifts at carbons bearing the substituent and at carbons ortho to the substituent correlated reasonably well with the Q parameter.A multiple regression analysis of chemical shifts with the field and resonance parameters of Swain and Lupton and the Q parameter produced significantly better correlations than those obtained when Q was omitted for these positions. 13C chemical shift correlations for carbons meta and para to the substituent were not significantly better than when Q was omitted.Significant correlations were obtained between field and resonance parameters and 13C chemical shifts of C-o and C-p, and C-i, C-o, C-m and C-p of the non-substituent bearing phenyl rings in ortho- and para-substituted phenyldiphenylamines, respectively.
Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties
Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai
, p. 9692 - 9704 (2021/11/30)
For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.
Optical and electrochemical effects of triarylamine inclusion to alkoxy BODIPY-based derivatives
Insuasty, Alberto,Madrid-Usuga, Duvalier,Mora-León, Ana G.,Ortiz, Alejandro,Rocha-Ortiz, Juan S.
, p. 18114 - 18123 (2021/10/12)
Three new triphenylamine-BODIPY dyadsBDPT1-3have been designed and synthesized. Their optoelectronic properties were investigated, which revealed strong electronic interactions between the donor and acceptor moieties, together with high sensitivity to the inclusion of alkoxy groups. The properties of the dyads were compared with those of reference compoundsAandBDP1, which exhibit broader absorption in the visible region as a result of the inclusion of donor groups and extended conjugation of the BODIPY core. Fluorescence quenching was also observed, which was attributed to the photoinduced electron transfer, evidenced from solvatochromic measurements, quantum yields and theoretical calculations. The oxidation potentials of new compounds were found to be lower when compared with those of other BODIPY analogues with donor groups attached. The redox, computational, absorbance and emission data suggest that compoundsBDPT1-3exhibit promising properties for their application in organic photovoltaic or light emitting (optoelectronic) devices.
