Mesoscopic helical architectures via self-assembly of porphyrin-based discotic systems

Abstract

Mesoscopic super-helices with preferred helicity have been serendipitously formed from the self-assembly of electroactive extended core discotic molecules. The investigation at dilute concentrations reveals intramolecular hydrogen-bonding and π-π stacking interactions as the driving force of the chiral self-assembly at different length scales.

Tuning the Organogelating and Spectroscopic Properties of a C3‐Symmetric Pyrene‐Based Gelator through Charge Transfer

“…Tris(3,3’‐diamido‐2,2’‐bipyridine)‐benzene‐1,3,5‐tricarboxamide‐based C 3 compounds exhibit a strong propensity to form highly ordered nanostructures through combined intramolecular H‐bonds and intermolecular π–π interactions [58–64] . On the other hand, pyrene is known to interact with electron‐poor molecules such as TNF [47–50] and TCNQ [68, 69] .…”

“…Intramolecular hydrogen bonding imparts BTABP monomers a rigid propeller‐shaped conformation, which allows their self‐assembly through π–π stacking [57] . Electro‐ and photoactive BTABP derivatives affording functional gels and supramolecular aggregates have been described with tetrathiafulvalene (TTF) [58–61] and porphyrin substituents [62, 63] . The attachment of pyrene units at the periphery of BTABP platform has been recently reported by some of us together with its gel formation ability [64] .…”

Large Synthetic Molecule that either Folds or Aggregates through Weak Supramolecular Interactions Determined by Solvent

“…51,52 The use of porphyrin rings as a peripheral arm in C 3 symmetric molecules can in principle allow formation of helical stacks with optical and electronic properties as reported by Elemans et al 53 More recently, Vela et al have investigated chiral and achiral tris(porphyrin) discotic C 3 derivatives based on the benzenetricarboxamide-bipyridine platform that stacks to give superhelical fibers. 54 On the other hand, it has been shown that introduction of chiral centers in the porphyrin moiety as well as metal ions can influence hierarchical transfer of chirality into a material morphology. 55…”

Redox‐Active Peptide‐Functionalized Quinquethiophene‐Based Electrochromic π‐Gel

“…Ubiquitously, the main objective is to assemble π‐conjugated units into a highly‐ordered superstructure for effective charge‐carrier mobility . Aromatic π‐conjugated aromatic cores at the centre functionalized with additional backbones self‐assemble into interesting functional supramolecular architectures . The π‐conjugated motifs have tendency to form supramolecular hierarchical functional nanostructures in a suitable solvent called as π‐gels, which was reported first time by Ajayaghosh et al .…”

“…[27] Aromatic pconjugated aromaticc ores at the centref unctionalized with additionalb ackbones self-assemble into interestingf unctional supramolecular architectures. [28][29][30] The p-conjugated motifs have tendency to form supramolecular hierarchical functional nanostructures in as uitables olvent called as p-gels, which wasr eported firstt imeb yA jayaghoshe tal. [31] Thereafter,t he classo f p-gelsw erer eporteda nd probed tremendously owing to their potentiala pplications in materials ciencesi ncluding organic electronics, sensing,O LED, energyh arvesting systems, memory effect,a nd imagingp robes.…”