Self-assembly and semiconductivity of an oligothiophene supergelator

Abstract

A bis(trialkoxybenzamide)-functionalized quaterthiophene derivative was synthesized and its self-assembly properties in solution were studied. In non-polar solvents such as cyclohexane, this quaterthiophene π-system formed fibril aggregates with an H-type molecular arrangement due to synergistic effect of hydrogen bonding and π-stacking. The self-assembled fibres were found to gelate numerous organic solvents of diverse polarity. The charge transport ability of such elongated fibres of quaterthiophene π-system was explored by the pulse radiolysis time resolved microwave conductivity (PR-TRMC) technique and moderate mobility values were obtained. Furthermore, initial AFM and UV-vis spectroscopic studies of a mixture of our electron-rich quaterthiophene derivative with the electron acceptor [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) revealed a nanoscale segregated assembly of the individual building blocks in the blend. 1070

Self‐Sorting in Supramolecular Assembly of π‐Systems

“…This fluorescence turns on/off features of super‐coiled ropes was utilized to detect various volatile aromatic compounds. Würthner and co‐workers revealed macroscopic self‐sorting of electron rich p‐type semiconducting oligothiophene based gelator (37) and n‐type semiconducting [6,6]‐phenyl C 61 butyric acid methyl ester (PCBM) . When p‐type and n‐type materials were mixed, they observed the nanoscale segregation.…”

Selbstorganisierte Gelbildner für die organische Elektronik

“…Die Entwicklung solcher weichen Materialien ist bedeutsam für den Entwurf energieeffizienter Funktionseinheiten. [43][44][45][46][47][48] Wie bereits erwähnt, zählen Thiophene zu den am häufigsten eingesetzten organischen heterogenen Bausteine für die Herstellung von leitfähigen Materialen. [40][41][42] Die gezielte Kontrolle des Selbstorganisationsprozesses während der Gelbildung ist jedoch eine Herausforderung.…”

“…In vielen Fällen wurden daher die Leitfähigkeiten sowohl von Filmen als auch von Nanostrukturen, die aus Lçsungen unterschiedlicher Substrate gebildet wurden, erforscht. [43][44][45][46][47][48] Wie bereits erwähnt, zählen Thiophene zu den am häufigsten eingesetzten organischen heterogenen Bausteine für die Herstellung von leitfähigen Materialen. Thiophene sind präparativ leicht zugänglich und weisen einzigartige optoelektronische, Redox-und Ladungstransporteigenschaften auf.…”

Macrocyclic Restriction with Flexible Alkylene Linkers: A Simple Strategy to Control the Solid‐State Properties of π‐Conjugated Systems

“…It is noteworthy that 3 forms a gel without any strong unidirectional intermolecular interaction, such as hydrogen bonds or dipole-dipole interactions, unlike other low-molecular-weight organic gelators. [12] As shown in Figure 3 a, scanning electron microscope (SEM) images of the dried gels of 3 showed intertwined network structures of microfibers, the morphologies of which depend on the solvent used for the gel formation. In EtOH, winding fibers with 0.1-0.5 mm widths form a complicated texture, while in EtOAc, straight whiskers with 0.3-3.0 mm widths construct a bundle structure (Figure 3 a).…”

“…[12] The powder XRD patterns of the dried gel and ground crystals of 3 are quite different from each other (Supporting Information). The crystals are most likely reconstructed through the solution in the equilibrium with the organogel.…”