33331-95-2Relevant academic research and scientific papers
Linear 1,4-coupled oligoanilines of defined length: Preparation and spectroscopic properties
Rozalska, Izabela,Kulyk, Paulina,Kulszewicz-Bajer, Irena
, p. 1235 - 1243 (2004)
A facile synthetic method involving SNAr coupling of 4-fluoronitrobenzene to arylamines, followed by reduction of the nitro groups, has been developed. The method allows the preparation of symmetric (NH 2/ NH2 end-capped) and asymmetric (Ph/NH2 end-capped) oligoanilines of even or odd chain lengths. The preparation of the NH2/NH2 end-capped trimer to octamer and Ph/NH2 end-capped trimer to pentamer is described. The effect of the chain length on the spectroscopic properties of the oxidized oligomers has been investigated by UV-Vis-NIR spectroscopy.
Healable supramolecular polymers as organic metals
Armao, Joseph J.,Maaloum, Mounir,Ellis, Thomas,Fuks, Gad,Rawiso, Michel,Moulin, Emilie,Giuseppone, Nicolas
, p. 11382 - 11388 (2014)
Organic materials exhibiting metallic behavior are promising for numerous applications ranging from printed nanocircuits to large area electronics. However, the optimization of electronic conduction in organic metals such as charge-transfer salts or doped conjugated polymers requires high crystallinity, which is detrimental to their processability. To overcome this problem, the combination of the electronic properties of metal-like materials with the mechanical properties of soft self-assembled systems is attractive but necessitates the absence of structural defects in a regular lattice. Here we describe a one-dimensional supramolecular polymer in which photoinduced through-space charge-transfer complexes lead to highly coherent domains with delocalized electronic states displaying metallic behavior. We also reveal that diffusion of supramolecular polarons in the nanowires repairs structural defects thereby improving their conduction. The ability to access metallic properties from mendable self-assemblies extends the current understanding of both fields and opens a wide range of processing techniques for applications in organic electronics.
Temperature Control of Sequential Nucleation–Growth Mechanisms in Hierarchical Supramolecular Polymers
Osypenko, Artem,Moulin, Emilie,Gavat, Odile,Fuks, Gad,Maaloum, Mounir,Koenis, Mark A. J.,Buma, Wybren Jan,Giuseppone, Nicolas
supporting information, p. 13008 - 13016 (2019/09/13)
Upon cooling insolution, chiral triarylamine tris-amide unimers produce organogels by stacking into helical supramolecular polymers, which subsequently bundle into larger fibers. Interestingly, circular dichroism, vibrational circular dichroism, and AFM imaging of the chiral self-assemblies revealed that monocolumnar P-helical fibrils formed upon fast cooling, whereas bundled M-superhelical fibers formed upon slow cooling. The mechanistic study of this structural bifurcation reveals the presence of a strong memory effect, reminiscent of a complex stepwise combination of primary and secondary nucleation-growth processes. These results highlight the instrumental role of sequential self-assembly processes to control supramolecular architectures of multiple hierarchical order.
Surface immobilized azomethine for multiple component exchange
Lerond, Michael,Bélanger, Daniel,Skene
, p. 6639 - 6646 (2017/10/06)
Diazonium chemistry concomitant with in situ electrochemical reduction was used to graft an aryl aldehyde to indium-tin oxide (ITO) coated glass substrates. This served as an anchor for preparing electroactive azomethines that were covalently bonded to th
Amino surface-functionalized tris(calix[4]arene) dendrons with rigid C 3-symmetric propeller cores
Gattuso, Giuseppe,Grasso, Giulia,Marino, Nino,Notti, Anna,Pappalardo, Andrea,Pappalardo, Sebastiano,Parisi, Melchiorre F.
experimental part, p. 5696 - 5703 (2011/11/29)
Dendrons composed of three functionalized cone calix[4]arene substructures covalently bound to rigid C3-symmetric tris-anilino cores through amide linkages have been obtained by a divergent synthetic protocol involving the coupling of p-nitrocalix[4]arene butanoic acid 9 with tris(4-aminophenyl) amine (TAPA), 1,3,5-tris(4-aminophenyl)benzene (TAPB), and 2,4,6-tris(4- aminophenyl)-s-triazine (TAPT). Two different amidation procedures were used to generate the dodecanitro intermediates (through activation of acid 9 with PyBOP catalyst or transformation into its acid chloride). The final reduction to the title dodecaamino dendrons was smoothly carried out with H2 and Raney-Ni catalyst.
