Hydrogen-Bonding Networks of Adamantane-Based Bisphenol Molecules: Toward the Preparation of Molecular Crystals with Channels

A series of adamantane-based bisphenol molecules with structurally related V-shaped skeletons were designed to examine the influence of molecular shapes and steric hindrances for the molecular association and packing of individual molecules in crystalline lattices. Single crystal X-ray analysis revealed that multiple intermolecular hydrogen bonds were formed between the hydroxyl groups of the phenol moieties. Crystallographic analysis of 1,3-bis(4-hydroxy-3,5-dimethylphenyl)adamantane (1) indicated the creation of a one-dimensional (1D) zigzag polymer through hydrogen bonds. In the crystals of 1,3-bis(3-bromo-4-hydroxyphenyl)adamantane (2), infinite 1D polymers composed of cyclic frameworks were sustained by intermolecular hydrogen bonds. 1,3-Bis(3-chloro-4-hydroxyphenyl)adamantane (3) and 1,3-bis(4-hydroxyphenyl)adamantane (4) formed frameworks with channels containing chloroform molecules in the solid state. Continuous 1D polymers consisting of cyclic frameworks were generated in crystals 3a and 4a, and these 1D polymers packed into two-dimensional (2D) layers with channel structures

Construction and Charge-Transfer Complexation of Adamantane-Based Macrocycles and a Cage with Aromatic Ring Moieties

Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C−H···π interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state

Hydrogen-Bonding Networks of Adamantane-Based Bisphenol Molecules: Toward the Preparation of Molecular Crystals with Channels

A series of adamantane-based bisphenol molecules with structurally related V-shaped skeletons were designed to examine the influence of molecular shapes and steric hindrances for the molecular association and packing of individual molecules in crystalline lattices. Single crystal X-ray analysis revealed that multiple intermolecular hydrogen bonds were formed between the hydroxyl groups of the phenol moieties. Crystallographic analysis of 1,3-bis(4-hydroxy-3,5-dimethylphenyl)adamantane (1) indicated the creation of a one-dimensional (1D) zigzag polymer through hydrogen bonds. In the crystals of 1,3-bis(3-bromo-4-hydroxyphenyl)adamantane (2), infinite 1D polymers composed of cyclic frameworks were sustained by intermolecular hydrogen bonds. 1,3-Bis(3-chloro-4-hydroxyphenyl)adamantane (3) and 1,3-bis(4-hydroxyphenyl)adamantane (4) formed frameworks with channels containing chloroform molecules in the solid state. Continuous 1D polymers consisting of cyclic frameworks were generated in crystals 3a and 4a, and these 1D polymers packed into two-dimensional (2D) layers with channel structures

Asymmetric Friedel–Crafts-Type Reaction of 2‑Vinylindoles to <i>N</i>‑Boc Imines Using a Chiral Imidazolidine-Containing NCN-Pincer Pd Catalyst

A chiral imidazolidine-containing NCN-pincer Pd-OTf complex (NCN-Pd cat) promoted the asymmetric nucleophilic addition of unprotected 2-vinylindoles to N-Boc imines in a Friedel–Crafts-type manner. The chiral (2-vinyl-1H-indol-3-yl)methanamine products become nice platforms for constructing multiple ring systems

Construction and Charge-Transfer Complexation of Adamantane-Based Macrocycles and a Cage with Aromatic Ring Moieties

Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C−H···π interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state

Hydrogen-Bonding Networks of Adamantane-Based Bisphenol Molecules: Toward the Preparation of Molecular Crystals with Channels

A series of adamantane-based bisphenol molecules with structurally related V-shaped skeletons were designed to examine the influence of molecular shapes and steric hindrances for the molecular association and packing of individual molecules in crystalline lattices. Single crystal X-ray analysis revealed that multiple intermolecular hydrogen bonds were formed between the hydroxyl groups of the phenol moieties. Crystallographic analysis of 1,3-bis(4-hydroxy-3,5-dimethylphenyl)adamantane (1) indicated the creation of a one-dimensional (1D) zigzag polymer through hydrogen bonds. In the crystals of 1,3-bis(3-bromo-4-hydroxyphenyl)adamantane (2), infinite 1D polymers composed of cyclic frameworks were sustained by intermolecular hydrogen bonds. 1,3-Bis(3-chloro-4-hydroxyphenyl)adamantane (3) and 1,3-bis(4-hydroxyphenyl)adamantane (4) formed frameworks with channels containing chloroform molecules in the solid state. Continuous 1D polymers consisting of cyclic frameworks were generated in crystals 3a and 4a, and these 1D polymers packed into two-dimensional (2D) layers with channel structures

Construction and Charge-Transfer Complexation of Adamantane-Based Macrocycles and a Cage with Aromatic Ring Moieties

Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C−H···π interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state

Construction and Charge-Transfer Complexation of Adamantane-Based Macrocycles and a Cage with Aromatic Ring Moieties

Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C−H···π interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state

Hydrogen-Bonding Networks of Adamantane-Based Bisphenol Molecules: Toward the Preparation of Molecular Crystals with Channels

A series of adamantane-based bisphenol molecules with structurally related V-shaped skeletons were designed to examine the influence of molecular shapes and steric hindrances for the molecular association and packing of individual molecules in crystalline lattices. Single crystal X-ray analysis revealed that multiple intermolecular hydrogen bonds were formed between the hydroxyl groups of the phenol moieties. Crystallographic analysis of 1,3-bis(4-hydroxy-3,5-dimethylphenyl)adamantane (1) indicated the creation of a one-dimensional (1D) zigzag polymer through hydrogen bonds. In the crystals of 1,3-bis(3-bromo-4-hydroxyphenyl)adamantane (2), infinite 1D polymers composed of cyclic frameworks were sustained by intermolecular hydrogen bonds. 1,3-Bis(3-chloro-4-hydroxyphenyl)adamantane (3) and 1,3-bis(4-hydroxyphenyl)adamantane (4) formed frameworks with channels containing chloroform molecules in the solid state. Continuous 1D polymers consisting of cyclic frameworks were generated in crystals 3a and 4a, and these 1D polymers packed into two-dimensional (2D) layers with channel structures

Construction and Charge-Transfer Complexation of Adamantane-Based Macrocycles and a Cage with Aromatic Ring Moieties

Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C−H···π interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state