Self-Assembling Carbohydrate-Functionalized Oligothiophenes

Abstract

Carbohydrate-functionalized oligothiophenes have been synthesized applying mild Sonogashira cross-coupling conditions. In an aqueous environment the amphiphilic hybrids self-assemble into chiral superstructures as a result of multiple hydrogen bond interactions and the helicity of the aggregates is controllable by the configuration of the carbohydrate unit. By means of atomic force microscopy highly ordered layer arrangements on substrates were characterized.

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

“…The UV–vis absorption spectrum of a thin film of 2 shows an asymmetric hypsochromic shift of the absorption peak (Fig. 2) indicative of the formation of weak H-aggregates in the solid state [34–35]. Thus, a hierarchical model for association can be developed in which the formation of hydrogen-bonded chains of 2 is followed by interchain H-aggregation, although this requires further experimental verification.…”

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

“…Av ariety of biomolecules such as peptides, [1,2] carbohydrates, [3][4][5] nucleobases [6,7] and nucleotides [8] haveb eenf unctionalized with semiconducting organic p-conjugated systemf or the synthesis of self-assembledn anostructuresw hichh ave beenu sedi nt he developmento fs upramolecular electronics. [9][10][11][12][13] Oligothiophene, [14][15][16][17][18] oligo(p-phenylenevinylene)( OPV), [19,20] diacetylene (DA), [21] benzo[ghi]perylenem onoimide (BPI), [22] naphthalened iimide (NDI) [23] andp erylened iimide (PDI) [24][25][26] have been conjugatedw ithv arious peptidem otifs.…”

Oligopeptide‐Assisted Self‐Assembly of Oligothiophenes: Co‐Assembly and Chirality Transfer

“…[1][2][3][4][5] Oligopeptides are one of the most attractive biomolecules to adjust the stacking mode of p-conjugated oligomers because of their structural variation and their ability to form various secondary structures, such as a-helices and b-sheets. [1][2][3][4][5] Oligopeptides are one of the most attractive biomolecules to adjust the stacking mode of p-conjugated oligomers because of their structural variation and their ability to form various secondary structures, such as a-helices and b-sheets.…”

“…Biomolecule-assisted self-assembly is an effective way to direct the self-assembly of extended p-conjugated oligomers and endow new functions. [1][2][3][4][5] Oligopeptides are one of the most attractive biomolecules to adjust the stacking mode of p-conjugated oligomers because of their structural variation and their ability to form various secondary structures, such as a-helices and b-sheets. [6][7][8] Extended p-conjugated oligomers, such as oligothiophenes [9][10][11][12][13][14][15][16][17][18][19][20][21] and oligo(p-phenylenevinylene)s, [22][23][24] have good electro-optical properties and show many potential applications.…”