[3.3]Orthocyclophanes with facing benzene and naphthalene rings

Mataka, Shuntarō; Takahashi, Kazufumi; Mimura, Takao; Hirota, Toshizumi; Takuma, Keisuke; Kobayashi, Hiroshi; Tashiro, Masashi; Imada, Kenjiro; Kuniyoshi, Minoru

doi:10.1021/jo00389a004

Cited by 36 publications

(10 citation statements)

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“…Approaches to compounds in which fused-or oligo-arenes are held in stacks include preparation of benzo-annelated bicyclo [4.4.1] undecanes, [54][55][56] quadruple-layered orthonaphthophanes, 52 and thieno [3.3]orthocyclophanes. 57 Whereas benzene undergoes oxidation at a relatively high potential to form poorly defined polymers, 58 these tripleand quadruple-decker analogs undergo oxidation to the radical cation and dication at relatively low potentials.…”

Section: Two-dimensional Compounds: π π π π-Stacking Interactionsmentioning

confidence: 99%

Stacked Conjugated Oligomers as Molecular Models to Examine Interchain Interactions in Conjugated Materials

2006

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Previous studies of the redox states of linear conjugated oligomers as models for polarons and bipolarons in conjugated polymers do not fully address the influence of intermolecular interactions on the electronic structure of conjugated systems in the solid state. Fusion of oligothiophenes onto a bicyclo[4.4.1]undecane core holds the conjugated oligomers in a permanent cofacial stack. One- and two-electron oxidation of the stacked oligomers affords mono(radical cation)s and dications that serve as models for polarons and bipolarons in p-doped conjugated polymers and demonstrates the effect of pi-stacking on the electronic structure of these species.

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Section: Two-dimensional Compounds: π π π π-Stacking Interactionsmentioning

confidence: 99%

Stacked Conjugated Oligomers as Molecular Models to Examine Interchain Interactions in Conjugated Materials

2006

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“…[14] The calculated distance between the centers of the neighboring quinoline rings of poly-1 a 10 ' is 4.2 , and the distance between the faces of the quinoline rings is 3.2 , which falls within the range of p-p interactions (Figure 5 b). [15] The vicinal quinoline units form two independent helices and the whole molecule forms a twisted-tape structure with a pitch of 40 (Figure 5 c).…”

Section: Adnaduplexisformedfromamultilayeredstructureofanmentioning

confidence: 99%

Construction of Helically Stacked π‐Electron Systems in Poly(quinolylene‐2,3‐methylene) Stabilized by Intramolecular Hydrogen Bonds

et al. 2020

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π‐Stacked polymers, which consist of layered π‐electron systems in a polymer, can be expected to be used in molecular electronic devices. However, the construction of a stable π‐stacked structure in a polymer is considerably challenging because it requires sophisticated designs and precise synthetic methods. Herein, we present a novel π‐stacked architecture based on poly(quinolylene‐2,3‐methylene) bearing alanine derivatives as the side chain, obtained through the living cyclo‐copolymerization of an o‐allenylaryl isocyanide. In the resulting polymer, the neighboring quinoline rings of the main chain form a layered structure with π–π interactions, which is stabilized by intramolecular hydrogen bonds. The vicinal quinoline units form two independent helices and the whole molecule is a twisted‐tape structure. This structure is established on the basis of UV/CD spectra, theoretical calculations, and atomic‐force microscopy.

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“…Accordingly, both the chemical structure and the three-dimensional arrangement have to be taken into account when developing new materials with optimal properties for optoelectronic applications. A number of cyclic oligomers, including [2,2]paracyclophane, [7][8][9][10][11][12] calix [4]arene, [13][14][15] bicyclo [4.4.1]undecane, [16][17][18] and pillar [5]arene, 19,20 have been used as scaffolds for the three-dimensional arrangement of p-conjugated systems. For example, Bazan et al [7][8][9] and Morisaki et al [10][11][12] independently reported that the [2,2]paracyclophane unit shows transannular through-space p-p interactions and is an excellent building block for the elongation of p-conjugated systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reaction, and optical properties of cyclic oligomers bearing 9,10-diphenylanthracene based on an aromatic tertiary amide unit

et al. 2014

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Novel cyclic aromatic amide oligomers containing highly fluorescent 9,10-diphenylanthracene units were prepared by condensation of a monomer with amino and ester functional groups using lithium bis(trimethylsilyl)amide. The cyclic trimer (C3A, 40%) and tetramer (C4A, 8%) were isolated using preparative gel permeation chromatography. Some of the aromatic proton signals derived from anthracene were observed in the upfield region (6.96-6.87 ppm) in the 1 H nuclear magnetic resonance spectrum of C3A. X-ray crystallographic analysis indicated that three anthracene moieties are inclined with respect to the cyclic skeleton and partly overlap each other. The fluorescence peak maximum of C3A (438 nm) showed a small red-shift compared with that of an acyclic model compound (425 nm).Reduction of the amide carbonyl group in C3A gave the cyclic trimer HC3A, which has a tertiary amine unit. The fluorescence peak maximum of HC3A (489 nm) was largely red-shifted from that of C3A and exhibited strong solvent dependence. A linear correlation was observed between the Stokes shift (Dn), ranging from 2981 to 6646 cm À1 , and the Reichardt's solvent polarity parameter [E T (30)].

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[3.3]Orthocyclophanes with facing benzene and naphthalene rings

Cited by 36 publications

References 0 publications

Stacked Conjugated Oligomers as Molecular Models to Examine Interchain Interactions in Conjugated Materials

Stacked Conjugated Oligomers as Molecular Models to Examine Interchain Interactions in Conjugated Materials

Construction of Helically Stacked π‐Electron Systems in Poly(quinolylene‐2,3‐methylene) Stabilized by Intramolecular Hydrogen Bonds

Synthesis, reaction, and optical properties of cyclic oligomers bearing 9,10-diphenylanthracene based on an aromatic tertiary amide unit

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