Exploiting the interactions of aromatic units for folding and assembly in aqueous environments

Abstract

A variety of non-covalent interactions (including hydrogen bonding, ionic interactions, metal coordination and desolvation/solvation) have been utilized to organize oligomers into well-defined structures. Herein is described a survey of aromatic foldamers that capitalize on electrostatic complementarity of substituted aromatic units to drive folding and assembly in aqueous environments. A brief description of recent advances in the understanding of aromatic interactions is provided, followed by examples of foldamers that exploit interactions between aromatic units to drive their assembly in predictable fashion. The history of our aromatic foldamers is traced from the first structure designed to fold into a pleated structure in an aqueous environment to a heteroduplex system more related to nucleic acids. Taken together, the results demonstrate that electrostatic complementarity of aromatic units provides a versatile framework for driving predictable folding and assembly in aqueous environments.

Structure determination of the tetracene dimer in helium nanodroplets using femtosecond strong-field ionization

“…1. In the previous experiments on CS 2 and OCS dimers, the probe pulse was sent at the peak of the alignment pulse, and no truncation was needed, because CS + 2 and OCS + ions can both survive the alignment field.…”

“…INTRODUCTIONNoncovalent interactions between aromatic molecules are crucial for many areas, such as molecular recognition, structure of macromolecules and organic solar cells. [1][2][3][4] At the most fundamental level, the interaction involves two aromatic molecules. This has been the subject of a large numbers of studies, often with a particular focus on determining the structure of the dimers.…”

Discrete π Stack of a Tweezer‐Shaped Naphthalenediimide–Anthracene Conjugate

“…[7][8][9][10][11][12][13][14][15][16][17][18][19] Among p-conjugated compounds, rylenediimides have been integratedt oa ssemble donor-acceptors ystemsf or energyand electron-transfer studies;t he discrete p stacks in covalent or self-assembled systemsh ave been also studied. [20][21][22][23][24][25][26] For instance,M atile and co-workersh ave utilized anion-p interactions to demonstratea nion transport and catalytic activity in naphthalenediimides (NDIs). [27,28] Würthner and co-workers have reported discrete p stacks in the aggregation of the related family of perylenediimides, based on the foldamer approach.…”

Anα-cyanostilbene derivative for the enhanced detection and imaging of amyloid fibril aggregates

“…Restriction to a planar conformation results in the expansion of electron-π conjugates, (i.e. the adjacent donor-π-acceptor electron bridges of 20 C=C bonds) and π-π stacking between benzene groups of dye molecules, all of which increase electron transfer and reduce the energy of the excited state [40][41][42] . Thus, the enhanced Stokes shift of ASCP is attributed to the addition of a methylpyridinium and dimethylamine moieties to the -cyanostilbene core of ASCP that enables an improved capacity to expand electron-p conjugates compared to that of ThT.…”