Abstract
Propagation and amplification of chirality are considered to play an important role in the chemical evolution of biological homochirality. Stereochemical communications have been demonstrated to have a significant effect on the formation of chiral hierarchical structures in helical polymers, surface assemblies and supramolecular polymers. The formation of supramolecular copolymers based on chiral and achiral bichromophoric perylenediimide (PDI) dyes having a binaphtyl- and biphenyl-core-bridging unit, respectively, was investigated in terms of chiral amplification and propagation. The biphenyl-bridged PDI dye was expected to perform as a prochiral component to adopt both right- and left-handed twisting structures with the free rotation over the phenyl-phenyl linkage upon partnered with the chiral binaphtly PDI dye in the coassemblies. The coassemblies between the chiral and achiral PDI dyes with dissimilar core units demonstrated the composition dependent control in the length of supramolecular nanofibers as well as amplification of optical activity.
Highlights
The origin of biological homochirality has been subject to debate and intrigued scientists for a long time
Introduction of a small amount of a chiral component in an assembly of achiral or prochiral molecules with an analogous structure successfully guides the one-handed global supramolecular chirality resulting in the chirality amplification as a consequence of “sergeants-and-soldiers” principle (Palmans et al, 1997; Smulders et al, 2008)
We investigate the coassembly of chiral Binaph-PDI with an achiral bichromophoric-PDI dye, Biph-PDI (Figure 1), possessing the dissimilar core
Summary
The origin of biological homochirality has been subject to debate and intrigued scientists for a long time. The hydrogels composed of a pair of oppositely charged peptides with the same chirality afforded the higher elastic modulus than the ones with heterochiral peptide pairs This result evokes the role of homochirality in collagen fibers in which the chirality propagates over hierarchy to construct collagen superhelices, leading to the unique mechanical properties of collagen tissues (Kadler et al, 2007). Chiral sergeant molecules and achiral soldier molecules share a common central selfassembling core unit with aromatic rings in the most cases of chirality amplification experiments, while the former component only tethers side-chains with point chirality. Such the chiral units in the periphery of the molecules successfully dictate the handedness in the rotational stacking of aromatic rings. The expression of sergeants-and-soldiers principle in the coassembly of chiral and achiral molecules with dissimilar self-assembling core units has been rarely demonstrated (Liu et al, 2015)
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