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Multiple Roles of 1,4-Diazabicyclo[2.2.2]octane in the Solvothermal Synthesis of Iodobismuthates.

ABSTRACT: Hybrid bismuth-containing halides are emerging as alternative candidates to lead-containing perovskites for light-harvesting applications, as Bi³⁺ is isoelectronic with Pb²⁺ and the presence of an active lone pair of electrons is expected to result in outstanding charge-carrier transport properties. Here, we report a family of one binary and three ternary iodobismuthates containing 1,4-diazabicyclo[2.2.2]octane (DABCO). These materials have been prepared solvothermally and their crystal structures, thermal stability, and optical properties determined. Reactions carried out in the presence of bismuth iodide and DABCO produced (C₆H₁₂N₂)BiI₃ (1), which consists of hybrid ribbons in which pairs of edge-sharing bismuth octahedra are linked by DABCO ligands. Short I···I contacts give rise to a three-dimensional network. Similar reactions in the presence of copper iodide produced (C₈H₁₇N₂)₂Bi₂Cu₂I₁₀ (2) and [(C₆H₁₃N₂)₂BiCu₂I₇](C₂H₅OH) (3) in which either ethylated DABCO cations (EtDABCO)⁺ or monoprotonated DABCO cations (DABCOH)⁺ are coordinated to copper in discrete tetranuclear and trinuclear clusters, respectively. In the presence of potassium iodide, a unique three-dimensional framework, (C₆H₁₄N₂)[(C₆H₁₂N₂)KBiI₆] (4), was formed, which contains one-dimensional hexagonal channels approximately 6 Å in diameter. The optical band gaps of these materials, which are semiconductors, range between 1.82 and 2.27 eV, with the lowest values found for the copper-containing discrete clusters. Preliminary results on the preparation of thin films are presented.

SUBMITTER: Cai Y

PROVIDER: S-EPMC8041286 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Sulfonylation of 1,4-Diazabicyclo[2.2.2]octane: Charge-Transfer Complex Triggered C-N Bond Cleavage.

Project description:A novel charge-transfer complex triggered sulfonylation of 1,4-diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge-transfer complex between electron-withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N-ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge-transfer complex formation between sulfonyl chlorides and DABCO, which facilitates the C-N bond cleavage of DABCO.

| S-EPMC6350051 | biostudies-literature

Synthesis, Antifungal Activity, and Biocompatibility of Novel 1,4-Diazabicyclo[2.2.2]Octane (DABCO) Compounds and DABCO-Containing Denture Base Resins.

Project description:The fungal pathogen Candida albicans causes a variety of oral infections, including denture stomatitis, which is characterized by inflammation of the oral mucosa in direct contact with dentures and affects a significant number of otherwise healthy denture wearers. While antifungal treatment reduces symptoms, infections are often recurrent. One strategy to address this problem is to incorporate compounds with fungicidal activities into denture materials to prevent colonization. Our laboratory synthesized novel derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO), which is an organic compound typically used as a catalyst in polymerization reactions. DABCO derivatives with different aliphatic chain lengths (DC16, DC16F, DC18, and C6DC16), as well as methacrylate monomers conjugated to DABCO compounds (DC11MAF and C2DC11MAF), were synthesized and tested for antimicrobial activity. All the compounds exhibited fungicidal activity against several Candida species at concentrations ranging between 2 and 4 μg/ml. Moreover, acrylic denture base resins fabricated to contain 1, 2, or 4 wt% DABCO compounds inhibited surface C. albicans biofilm formation, as well as fungal growth, in disc diffusion assays. Remarkably, discs (4 wt%) aged for 2 months also exhibited approximately 100% growth-inhibitory activity. While some DABCO compounds exerted intermediate to high cytotoxicity against mammalian oral cell types, DC11MAF and denture base resin discs containing 2 or 4 wt% C2DC11MAF exhibited relatively low cytotoxicity against periodontal ligament (PDL) cell and gingival fibroblast (GF) lines, as well as primary oral epithelial cells. These studies demonstrate that DABCO derivatives can be incorporated into denture materials and exert fungicidal activity with minimal cytotoxicity to mammalian cells. DC11MAF and C2DC11MAF are considered strong candidates as therapeutic or preventive alternatives against Candida-associated denture stomatitis.

| S-EPMC5365721 | biostudies-literature

1,4-Diazo-niabicyclo-[2.2.2]octane terephthalate.

Project description:In the title compound, C(6)H(14)N(2+)·C(8)H(4)O(4) (2-), the protonated 1,4-diazo-niabicyclo-[2.2.2]octane cations and the deprotonated terephthalate anions are alternately linked by N-H?O hydrogen bonds into chains.

| S-EPMC2960572 | biostudies-literature

N-Alkylated 1,4-Diazabicyclo[2.2.2]octane-Polyethylene Glycol Melt as Deep Eutectic Solvent for the Synthesis of Fisher Indoles and 1<i>H</i>-Tetrazoles.

Project description:1,4-Diazabicyclo[2.2.2]octane (DABCO)-based ionic liquids (ILs) 2-4 were synthesized by the N-alkylation of DABCO using alkyl halides of varying chain lengths (C2, C5, and C7). The N-alkylated DABCO-ILs were mixed with polyethylene glycols (PEGs) of varying molar masses as hydrogen bond donors (HBDs) to prepare new deep eutectic solvents (DESs). These DABCO-PEG-based DESs were successfully employed for the synthesis of a variety of indoles 7a-7h (by Fischer indole synthesis) and 1H-tetrazoles 9a-9i (by click chemistry). For comparison, DESs of DABCO-ILs with different alcohols (as HBD) were also prepared and investigated for the synthesis of indoles. Although comparable yields were observed in DES-containing alcohols and PEGs, the use of PEG as HBD in DES (as an alternative to alcohols) provides a much safer, nonvolatile, and environmentally benign reaction medium for synthetic reactions. The first successful application of PEG-polymer-based DES as benign reaction media for organic syntheses offers exciting opportunities to be explored in the realm of green synthesis.

| S-EPMC6641132 | biostudies-literature

Systematic study of the substitution effect on the tetrel bond between 1,4-diazabicyclo[2.2.2]octane and TH<sub>3</sub>X.

Project description:A tetrel bond was characterized in the complexes of 1,4-diazabicyclo[2.2.2]octane (DABCO) with TH3X (T = C, Si, Ge; X= -Me, -H, -OH, -NH2, -F, -Cl, -Br, -I, -CN, -NO2). DABCO engages in a weak tetrel bond with CH3X but a stronger one with SiH3X and GeH3X. SiH3X is favorable to bind with DABCO relative to GeH3X, inconsistent with the magnitude of the σ-hole on the tetrel atom. The methyl group in the tetrel donor weakens the tetrel bond but an enhancing effect is found for the other substituents, particularly -NO2. The substitution effect is also related to the nature of the tetrel atom. The halogen substitution from F to I has a weakening effect in the CH3X complex but an enhancing effect in the SiH3X complex and a negligible effect in the GeH3X complex. The above abnormal results found in these complexes can be partly attributed to the charge transfer from the lone pair on the nitrogen atom of DABCO into the anti-bonding orbital σ*(T-X) of TH3X. The stability of both SiH3X and GeH3X complexes is primarily controlled by electrostatic interactions and polarization.

| S-EPMC9064731 | biostudies-literature

Self-Assembling Metallocomplexes of the Amphiphilic 1,4-Diazabicyclo[2.2.2]octane Derivative as a Platform for the Development of Nonplatinum Anticancer Drugs.

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| S-EPMC8793087 | biostudies-literature

1,4-Diazo-niabicyclo-[2.2.2]octane tetra-chloridozincate monohydrate.

Project description:In the title compound, (C(6)H(14)N(2))[ZnCl(4)]·H(2)O, the crystal packing is governed by an extensive three-dimensional network of N-H⋯Cl, N-H⋯O and O-H⋯Cl hydrogen bonds. The zinc(II) metal centre has a slightly distorted tetra-hedral coordination geometry.

| S-EPMC2977617 | biostudies-literature

1,4-Diazo-niabicyclo-[2.2.2]octane tetra-bromidocadmate(II) monohydrate.

Project description:The metal atom in the anion of the title salt, (C(6)H(14)N(2))[CdBr(4)]·H(2)O, shows a slightly distorted tetra-hedral coordination. The water mol-ecule is involved in three hydrogen bonds, viz. one N-H?O and two O-H?Br, and an N-H?Br inter-action consolidates the three-dimensional network.

| S-EPMC2977123 | biostudies-literature

1,4-Diazo-niabicyclo-[2.2.2]octane bis-(2,4,6-trinitro-phenolate).

Project description:In the title compound, C(6)H(14)N(2) (2+)·2C(6)H(2)N(3)O(7) (-), the cation possesses crystallographically imposed twofold rotation symmetry. In the crystal structure, the cation and anions are linked into a trimeric aggregate by inter-molecular N-H⋯O hydrogen bonds. The trimeric units are further connected by π-π inter-actions [centroid-centroid distances = 3.507 (2)-3.660 (3) Å], forming layers parallel to the bc plane.

| S-EPMC3006919 | biostudies-literature

1,4-Diazo-niabicyclo-[2.2.2]octane tetra-chloroiodate(III) chloride.

Project description:In the title compound, C(6)H(14)N(2) (2+)·Cl(4)I(-)·Cl(-), the dication and the anions lie on special positions. The dication has mm2 symmetry with two bonded C atoms and the two N atoms located on a crystallographic mirror plane parallel to bc, and with a mirror plane parallel to ab passing through the mid points of the three C-C bonds. In the square-planar Cl(4)I(-) anion, two Cl atoms and the I atom are located on the mm2 axis; the other two Cl atoms are disordered over two postions of equal occupancy (0.25) across the mirror parallel to the ab plane. The Cl(-) anion is located on the mm2 axis. The crystal structure is stabilized by inter-molecular N-H⋯Cl hydrogen bonds.

| S-EPMC2983961 | biostudies-literature

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