Light-triggered self-construction of supramolecular organic nanowires as metallic interconnects

Faramarzi, Vina; Niess, Frédéric; Moulin, Émilie; Maaloum, Mounir; Dayen, Jean‐François; Beaufrand, Jean Baptiste; Zanettini, Silvia; Doudin, B.; Giuseppone, Nicolas

doi:10.1038/nchem.1332

Cited by 169 publications

(182 citation statements)

References 46 publications

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“…In addition, a more rigid core is likely to induce stronger interstack ordering, which may lead to the formation of nanowires. Such nanostructures have been extensively developed for triarylamines22b–22e and observed recently in other oligo(aniline)‐based systems 13…”

Section: Resultsmentioning

confidence: 97%

Exploring Redox States, Doping and Ordering of Electroactive Star‐Shaped Oligo(aniline)s

Mills

Fey

Marszałek

et al. 2016

Chemistry A European J

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We have prepared a simple star‐shaped oligo(aniline) (TDPB) and characterised it in detail by MALDI‐TOF MS, UV/Vis/NIR spectroscopy, time‐dependent DFT, cyclic voltammetry and EPR spectroscopy. TDPB is part of an underdeveloped class of π‐conjugated molecules with great potential for organic electronics, display and sensor applications. It is redox active and reacts with acids to form radical cations. Acid‐doped TDPB shows behaviour similar to discotic liquid crystals, with X‐ray scattering investigations revealing columnar self‐assembled arrays. The combination of unpaired electrons and supramolecular stacking suggests that star‐shaped oligo(aniline)s like TDPB have the potential to form conducting nanowires and organic magnetic materials.

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Section: Resultsmentioning

confidence: 97%

Exploring Redox States, Doping and Ordering of Electroactive Star‐Shaped Oligo(aniline)s

Mills

Fey

Marszałek

et al. 2016

Chemistry A European J

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“…As it was previously demonstrated that one-dimensional self-assembled structures of TPA derivatives formed by photoirradiation have conductivity along the assembly axis 19,[46][47][48] , we also investigated the current-voltage relationship of the self-assembled structures of 1, to determine the effect of supramolecular chirality and photopolymerization of the DA moieties on conductivity ( Supplementary Fig. 12).…”

Section: Conductivity Measurementmentioning

confidence: 99%

“…As a key molecular motif for the light-induced self-assembly process, we use a triphenylamine (TPA) moiety that contains three phenyl rings connected to a central nitrogen atom similar to the blades of a propeller. TPA-containing molecules have been shown to selfassemble on light exposure in chlorinated solvents by the formation of triphenylammonium radicals that adopt more planar configurations than the neutral forms and facilitate stacking [19][20][21][22][23] . Simply by employing CPL as a light source in the self-assembly process of a TPA-containing molecule, we show that self-assembled aggregates with supramolecular chirality can be generated, driven by the helical stacking of the TPA moieties.…”

mentioning

confidence: 99%

Induction and control of supramolecular chirality by light in self-assembled helical nanostructures

et al. 2015

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Evolution of supramolecular chirality from self-assembly of achiral compounds and control over its handedness is closely related to the evolution of life and development of supramolecular materials with desired handedness. Here we report a system where the entire process of induction, control and locking of supramolecular chirality can be manipulated by light. Combination of triphenylamine and diacetylene moieties in the molecular structure allows photoinduced self-assembly of the molecule into helical aggregates in a chlorinated solvent by visible light and covalent fixation of the aggregate via photopolymerization by ultraviolet light, respectively. By using visible circularly polarized light, the supramolecular chirality of the resulting aggregates is selectively and reversibly controlled by its rotational direction, and the desired supramolecular chirality can be arrested by irradiation with ultraviolet circularly polarized light. This methodology opens a route to ward the formation of supramolecular chiral conducting nanostructures from the self-assembly of achiral molecules.

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“…Intriguingly such devices display low resistances, with ohmic-like current-voltage, I-V, characteristics. This points to the nanowires being good charge conductors, 4 i.e. being potentially useful for electronic applications.…”

Section: Sandip Bhattacharya* Akinlolu Akande and Stefano Sanvitomentioning

confidence: 99%

Spin transport properties of triarylamine-based nanowires

2014

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Triarylamine-derivatives can self-assemble upon light irradiation in onedimensional nanowires with remarkable hole transport properties.We use a combination of density functional theory and Monte Carlo simulations to predict the nanowires spin-diffusion length. The orbital nature of the nanowires valence band, namely a singlet p-like band localised on N, suggests that hyperfine coupling may be weak and that spin-orbit interaction is the primary source of intrinsic spin relaxation.Thus, we construct a model where the spin-orbit interaction mixes the spins of the valence band with that of three degenerate lower valence bands of sp 2 nature. The model includes also electron-phonon interaction with a single longitudinal mode. We find a room temperature spin-diffusion length of the order of 100 nm, which increases to 300 nm at 200 K. Our results indicate that triarylamine-based nanowires are attractive organic semiconductors for spintronics applications.Functionalized triarylamines are a family of molecules well known in organic electronic applications such as light-emitting diodes, field-effect transistors and more recently multilayered heterojunctions solar cells. 1,2 Triarylamine derivatives dispersed in chloroform solution, when exposed to light, self-assemble in one dimensional (1D) supramolecular nanowire structures. 3 Even more interesting is the fact that the nanowires can be grown across nanogaps so that two-terminal self-assembled devices can be made. Intriguingly such devices display low resistances, with ohmic-like current-voltage, I-V, characteristics. This points to the nanowires being good charge conductors, 4 i.e. being potentially useful for electronic applications.In this communication we report on a first principle calculation of the spin-diffusion length of one of such nanowires, i.e. we provide an assessment on whether or not triarylamines derivatives can be used as materials platform for organic spintronics. 5 In particular, we focus on nanowires forming from the precursor depicted in Fig. 1(a), for which hole transport experimental data are available, 4 and for which we have recently estimated 6 room temperature hole mobility of the order of 10 cm 2 V À1 s À1 , for a pristine defect free nanowire structure.The electronic structure of the molecule in the gas phase is calculated by using density functional theory (DFT), at the level of the hybrid B3LYP functional, 7 for the molecule's geometry optimized by conjugate gradient (to forces smaller than 2 Â 10 À5 Hartree per Bohr). In particular we use the DFT numerical implementation of the Gaussian09 suit 8 and the 6-31G* basis set. We obtain a gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of 4.1 eV. Most importantly for the discussion here the HOMO is an orbital singlet strongly localized on the central N atom of the triarylamine unit. An orbital decomposition reveals its strong p z character, as demonstrated by the charge density isosurface of Fig. 1(b). Note that the orbital character...

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Light-triggered self-construction of supramolecular organic nanowires as metallic interconnects

Cited by 169 publications

References 46 publications

Exploring Redox States, Doping and Ordering of Electroactive Star‐Shaped Oligo(aniline)s

Exploring Redox States, Doping and Ordering of Electroactive Star‐Shaped Oligo(aniline)s

Induction and control of supramolecular chirality by light in self-assembled helical nanostructures

Spin transport properties of triarylamine-based nanowires

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