2016
DOI: 10.1021/acs.accounts.6b00038
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Folding of ortho-Phenylenes

Abstract: In nature, the folding of oligomers and polymers is used to generate complex three-dimensional structures, yielding macromolecules with diverse functions in catalysis, recognition, transport, and charge- and energy-transfer. Over the past 20-30 years, chemists have sought to replicate this strategy by developing new foldamers: oligomers that fold into well-defined secondary structures in solution. A wide array of abiotic foldamers have been developed, ranging from non-natural peptides to aromatics. The ortho-p… Show more

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Cited by 100 publications
(134 citation statements)
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“…[30] Indeed, it is admitted that there is a better delocalisation of π-electrons following the para/ortho/meta sequence and numbers of studies have tried to elucidate the origin of the restricted π-conjugation between para, ortho and meta substituted oligophenylenes. [30][31][32][33][34][35][36] In our case, it is clear that 3 displays a different behaviour compared to its building block meta terphenyl as it presents a relatively intense degree of conjugation between the phenyl and the fluorene. Thus, the 'linkage' effect cannot explain by itself this feature and other parameters should be invoked.…”
Section: Scheme 1 Synthetic Routes To 1 Andmentioning
confidence: 67%
“…[30] Indeed, it is admitted that there is a better delocalisation of π-electrons following the para/ortho/meta sequence and numbers of studies have tried to elucidate the origin of the restricted π-conjugation between para, ortho and meta substituted oligophenylenes. [30][31][32][33][34][35][36] In our case, it is clear that 3 displays a different behaviour compared to its building block meta terphenyl as it presents a relatively intense degree of conjugation between the phenyl and the fluorene. Thus, the 'linkage' effect cannot explain by itself this feature and other parameters should be invoked.…”
Section: Scheme 1 Synthetic Routes To 1 Andmentioning
confidence: 67%
“…This feature is of great importance as very often an ortho linkage leads to a strong steric hindrance, which in turn can break the conjugation. 3,36,68,78,79 This feature can be exemplified with the terphenyl molecules possessing either a para or an ortho linkage (figure 5, left).…”
Section: Origin Of the π-Conjugation Breakingmentioning
confidence: 99%
“…Recreating this feature on synthetic systems would not only allow reproducing biological functions but also developing new functions that align with our technological needs. This has inspired the development of conformationally ordered synthetic oligomers known as foldamers12345678, which are able to adopt folded conformations through non-covalent intramolecular interactions encoded in their primary structure. In the last years, there have been remarkable advances in the design of foldamers that self-assemble into well-defined structural motifs12345678, such as helices, pillars and sheets, among others.…”
mentioning
confidence: 99%
“…This has inspired the development of conformationally ordered synthetic oligomers known as foldamers12345678, which are able to adopt folded conformations through non-covalent intramolecular interactions encoded in their primary structure. In the last years, there have been remarkable advances in the design of foldamers that self-assemble into well-defined structural motifs12345678, such as helices, pillars and sheets, among others. Many foldamers have been explored in diverse fields including protein mimicking9101112131415, molecular recognition161718, self-assembly192021, and photoinduced electron and energy transfer22232425, with very promising results.…”
mentioning
confidence: 99%