Acid-induced formation of hydrogen-bonded double helix based on chiral polyphenyl-bridged bis(2,2′-bipyridine) ligands

Sham, Kiu‐Chor; Yee, Chi‐Chung; Pan, Yi; Lau, Kai‐Chung; Yiu, Shek‐Man; Kwong, Hoi‐Lun

doi:10.1039/c4ra00849a

Cited by 11 publications

(5 citation statements)

References 51 publications

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“…(C) Formation of a hydrogen-bonded double-stranded helix ([( 272 ) 2 H 2 ](ClO 4 ) 2 ) and a space-filling model of the X-ray crystal structure of [( 272 ) 2 H 2 ](FeCl 4 ) 2 . (Reproduced with permission from ref . Copyright 2014 The Royal Society of Chemistry.)…”

Section: Multistranded Helical Assembliesmentioning

confidence: 61%

“…Wisner and co-workers synthesized an alternate ADADA pentamer ( 270 ) and AADD tetramer ( 271 ) using a pyridine unit, and 1,4-thiazine-1,1-dioxide and indole units as a hydrogen acceptor (A) and donor (D), respectively (Figure B). , 270 and 271 self-assembled to form homodouble helices via intermolecular hydrogen bonding interactions supported by 2D 1 H NMR and X-ray crystallographic analyses. Kwong and co-workers found that a chiral biphenylene-linked bis(2,2′-bipyridine) ( 272 ) forms a homodouble helix upon monoprotonation of the terminal bipyridine residues in the presence of HClO 4 , assisted by the interior interstrand hydrogen bonds together with exterior CH/Cl hydrogen bonds between ClO 4 – and the two ligand strands (Figure C) . The single-crystal X-ray analysis of its model, [( 272 ) 2 H 2 ](FeCl 4 ) 2 , supports such a doubly hydrogen-bonded double-helical structure.…”

Section: Multistranded Helical Assembliesmentioning

confidence: 83%

“…448,449 − and the two ligand strands (Figure 84C). 450 The single-crystal X-ray analysis of its model, [(272) 2 H 2 ](FeCl 4 ) 2 , supports such a doubly hydrogen-bonded double-helical structure.…”

Section: Multistranded Helical Assembliesmentioning

confidence: 99%

“…693,694 However, the enantioselective synthesis of helical polymers based on the magnetochiral dichroism mechanism has not been reported. Recently, Zou et al demonstrated for the first time the enantioselective synthesis of a helical PDA in the liquid crystalline phase with linearly polarized light (LPL) in a parallel or antiparallel magnetic field (Figure 132Bb) using a disc- shaped mesogenic diacetylene derivative (451), in which three diacetylene units (450) are noncovalently linked to a 1,3,5trisubstituted benzene core (449) through hydrogen bonding (Figure 132Ba and d). 695 The preferred-handed helix sense of the helical PDA chain can be controlled with the relative orientation of LPL and the magnetic field, as confirmed by almost mirror-image CD signals (Figure 132Bc).…”

Section: Chart 34mentioning

confidence: 99%

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Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.

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Section: Multistranded Helical Assembliesmentioning

confidence: 61%

Section: Multistranded Helical Assembliesmentioning

confidence: 83%

Section: Multistranded Helical Assembliesmentioning

confidence: 99%

Section: Chart 34mentioning

confidence: 99%

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Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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“…The polyphenyls are widely used in drug synthesis, organic synthesis, heat exchanger, and so forth, (more details can be referred to Galmiche et al [13], Devrim [14], Sham et al [15], Pritchard et al [16] and Fujii et al [17]), and also biphenyl compounds have their extensive industrial applications (see Ryu et al [18], Olivas et al [19], Sari et al [20], Bawana et al [21] and Borji et al [22]). For instance, 4,4-bis (chloromethyl) biphenyl used for the synthesis of brightening agents, and polychlorinated biphenyls as dangerous organic pollutants and lead to global pollution which is applied in print and dyeing extensively.…”

Section: Introductionmentioning

confidence: 99%

Topological indices computing on random chain structures

Shi

Gao

2020

Int J of Quantum Chemistry

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Topological indices are a vital tool in QSAR/QSPR study, and Randić index and Zagreb index are mostly historical and well‐known indices which have been widely used to predict the properties of compounds. In recent years, to meet the demands from various engineering applications, some variants of Randić index and Zagreb index are defined and investigated. In this work, we determine the redefined Zagreb indices, forgotten index, reduced reciprocal Randić index and reduced second Zagreb index for random polyphenyl chain and random spiro chain which are produced by zeroth‐order Markov process and frequently appears in the field of materials and pharmacology. Furthermore, the average values and special settings in p1 or p2 to be zero are discussed.

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Structure and Property Diversity of Chiral Helicene Oligomers

Saito

Shigeno

Yamaguchi

2015

Encyclopedia of Polymer Science and Technology

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alkylthio, and perfluoroalkyl groups. In addition, cyclization of helicene oligomers provides another method of obtaining diversity.A notable aspect in the diversity of helicene oligomers is that they can be connected to provide multidomain oligomers (Fig. 4). When two helicene oligomers are connected, they are referred to herein as homo-bidomain oligomers. Cyclic homo-bidomain oligomers are also conceivable. Hetero-multidomain oligomers can be obtained by connecting different structures of oligomers. Such manipulations provide a large diversity of structures.Because helicene can generate characteristic π−π interactions, helicene oligomers often form bimolecular, trimolecular, tetramolecular, and polymolecular aggregates in which homoaggregation and heteroaggregation can also occur. Such aggregates self-assemble to form fibrils, vesicles, liquid crystals, and surface monolayers. These noncovalent bonding interactions provide diversity of the structure of helicene oligmers. Diverse Properties of Helicene OligomersStructural diversity is directly related to diversity of properties, and the properties of a helicene oligomer can be varied by structural modifications. In addition, multidomain oligomers can be designed, in which properties A and B of each domain can be combined. Such compounds exhibit property A + B or even another property C, a result regarded as the "synthesis of a property or function." Aggregation and self-assembly of helicene oligomers further increase property diversity, which covers materials with a broad range of sizes from subnanometersized molecules through nano-and micrometer-sized molecular aggregates and molecular self-assemblies to macroscopic bulk materials. Helicene oligomers are sensitive to changes in the environment such as temperature, solvent, and concentration. Different properties appear in dilute solution, in concentrated Amidohelicene oligomers: (a) acylcic oligomers (P)-1 (n = 1−9) with dianiline spacer, cyclic oligomers (P)-2 (n = 1−10) with dianiline spacer, (b) acyclic oligomers (P)-3 (n = 1−9) with m-phenylene spacer, and acyclic reverse oligomers (P)-4 (n = 1−4). (c) Schematic representation of reversible change between helix dimer and random coils of (P)-3 and (P)-4. solution, in the crystalline state, in the amorphous state, on the solid surface, at the solid-liquid interface, in fiber assemblies, in liquid crystals, and in gels. Dynamic properties of helicene oligomers are also interesting, and structural changes are largely affected by the environment, providing a stimulus response or possible molecular switching materials. It is also noteworthy that the process of a structure change can produce unusual transient phenomena. Amidohelicene OligomersStudies on helicene oligomers were initiated with amide derivatives (Fig. 5a, top), in which the spacer has a bent shape and includes both hydrogen bonding donor and acceptor moieties (24). (P)-5,8-Helicenedicarboxylate was reacted with bis(2,6-dimethylanilino)cyclohexane to give a series of acyclic helicene oligomers 1 up t...

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Acid-induced formation of hydrogen-bonded double helix based on chiral polyphenyl-bridged bis(2,2′-bipyridine) ligands

Cited by 11 publications

References 51 publications

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Topological indices computing on random chain structures

Structure and Property Diversity of Chiral Helicene Oligomers

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