Self-assembly of hydrogen-bond assisted supramolecular azatriphenylene architectures

Microwave-Assisted Synthesis and Properties of Novel Hexaazatrinaphthylene Dendritic Scaffolds

“…Considering the width of the fibers (30-40 nm), the fibrilar structures most probably comprise of several single stacks in an "edge-on" arrangement and parallel assembled. These hypotheses may point to a compromise between two main driving forces in the self-assembly of the compounds, namely the π-stacking interfacial interactions (involved in the aromatic cores of G1 within a single column) and the hydrogen bonding of amine side groups (which promote the intercolumnar packing) [20,21].…”

“…Firstly, particles around 12-25Ǻ in size and 3Ǻ width appeared randomly distributed on the surface. Secondly, fibers [20] (30-40 nm in size and 4-6Ǻ width) developed in the material. The number and length of these fibers were increased at longer times of immersion.…”

Rational synthesis of bis(hexyloxy)-tetra(hydroxy)-triphenylenes and their derivatives

“…Similarly, multiple different functionalities can be introduced at several points in the synthesis, providing facile routes to mixed triphenylene derivatives with twoor moretypes of substituents. The synthetic routes demonstrated herein can likely be adapted to the preparation of heterocyclic triphenylene derivatives such as azatriphenylenes, [36][37][38][39] which are known to exhibit different electronic and physical properties 36,37 than triphenylene derivatives but their development has been limited by the current use of toxic and costly transition metal catalysts in their synthesis. 38,39 In general, we anticipate triphenylene derivatives will continue to play vital roles in the development of multifunctional mesogens with implications in such areas as organic electronic and photovoltaic materials, and rational routes to multifunctional triphenylene derivatives, such as those described herein, will allow the full potential of these unique compounds to be explored and applied.…”

Hydrogen-bonded Supramolecular π-Functional Materials

“…Since the first article by Schoonbeek et al in 1999, where mono- and bithiophene bearing pendant alkylureas were organized into fibers that displayed improved charge transport features, the self-assembling properties of several organic semiconductors functionalized with amide or urea groups have been studied. Recent examples include aromatic amines like phenothiazine or carbazol, electronically rich entities like tetrathiofulvalene (TTF), discotic molecules such as hexabenzocoronene (HBC), phthalocyanine (Pcs) or porphyrin (Pp), fused aromatics like pyrene, perylene bisimide (PBI), triphenylenes, or azatriphenylenes, and conjugated oligomers like oligophenylenevinylene (OPV), oligofluorene (OF) , or oligothiophene (OT), , among others. The principal aim is to increase the stability of the stacks and to enhance the degree of order of the stacking molecules within a single column, since it has been demonstrated that the charge-carrier mobility and hence the performance of optoelectronic devices, such as field-effect transistors (FETs), light-emitting diodes (LEDs), and photovoltaic cells, depends to a large extent on this parameter .…”