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Synthesis of Triptycene-Based Organosoluble, …
A series of triptycene-derived Tröger's bases with molecular clip shaped structures have been conveniently and efficiently synthesized by one-pot condensation of corresponding amino-substituted triptycenes with paraformaldehyde in the presence of trifluoroacetic acid, and their structures have been characterized by NMR, MALDI-TOF MS spectra, elemental analyses and single-crystal X-ray diffraction.
Synthetic efforts to mimic the active sites of these diiron enzymes, such as that in soluble methane monooxygenase hydroxylase (sMMOH) (), have generated a diverse assortment of model compounds,– but reproducing both the structure and function of the carboxylate-bridged diiron unit in a single biomimetic platform has not yet been achieved. To obtain more accurate diiron protein models, we have designed advanced ligand frameworks that are sufficiently pre-organized to afford the desired coordination geometry upon metallation with iron salts.– Ultimately, we wish to construct a diiron compound having two syn N-donors, an oxygen-rich environment, and a covalently-tethered bridging carboxylate, and which can hydroxylate hydrocarbons under mild conditions using O2.
Synthesis of dihydroxy triptycene - [DOCX Document]
A novel triptycene-based ligand with a pre-organized framework was designed to model carboxylate-bridged diiron activesites in bacterial multicomponent monooxygenase (BMM) hydroxylase enzymes. The synthesis of the bis(benzoxazole)-appended ligand L1 depicted was accomplished in 11 steps. Reaction of L1 with iron(II) triflate and a carboxylate source afforded the desired diiron(II) complex [Fe2L1 (μ-OH) (μ-O2CArTol)(OTf)2].
A readily scalable route with high synthetic efficiency is desired in order to prepare gram-quantity of L1. A four-step column-free synthesis of 1,8-dihydroxytriptycene (DHT) (4) was accomplished starting from the commercially available reagent 1,8-dihydroxyanthraquinone. As shown in , methylation of 1,8-dihydroxyanthraquinone using dimethyl sulfate (~3.5 equiv) gave 1,8-dimethoxyanthraquinone (1) in 95% yield. Crude 1 was directly reduced by zinc dust in refluxing 10% aqueous NaOH, affording 1,8-dimethoxyanthracene (2) in 96% yield after recrystallization from DCM. To minimize the potentially explosive benzyne intermediate generated during the Diels-Alder reaction in the next step, only ~5 g of precursor 2 was used each time in the reaction. After several runs, the combined crude mixture was subjected to crystallization from acetone, affording 1,8-dimethoxytriptycene (3) in 67% yield. Lastly, deprotection of 1,8-dimethoxytriptycene (3) using BBr3 in anhydrous DCM, after recrystallization from acetone, gave pure 1,8-dihydroxytriptycene (DHT, 80%) (4). This four-step column-free synthesis afforded 4 in 49% overall yield.
Synthesis of soluble and thermally stable triptycene …
Hsiao, Sheng-Huei; Liao, Yu-Chuan. 2017. "Facile Synthesis of Electroactive and Electrochromic Triptycene Poly(ether-imide)s Containing Triarylamine Units via Oxidative Electro-Coupling." Polymers 9, no. 10: 497.
Hsiao S-H, Liao Y-C. Facile Synthesis of Electroactive and Electrochromic Triptycene Poly(ether-imide)s Containing Triarylamine Units via Oxidative Electro-Coupling. Polymers. 2017; 9(10):497.
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Synthesis of triptycene based non-conjugated …
Hsiao, S.-H.; Liao, Y.-C. Facile Synthesis of Electroactive and Electrochromic Triptycene Poly(ether-imide)s Containing Triarylamine Units via Oxidative Electro-Coupling. Polymers 2017, 9, 497.
Design and Synthesis of a Novel Triptycene-based …
My research interest is focusing on the synthesis of non-planar porphyrins and triptycene molecular scaffolds and the determination of structure using X-ray diffraction crystallography to study their conformation, alignments and related properties.
13/01/2018 · Triptycene Derivativ..
Undergraduate students, graduate students, and postdoctoral researchers are exposed to a diverse array of topics including organic chemistry, synthesis, bioorganic chemistry, macromolecular structure (nucleic acids and proteins), biochemistry, and polymer chemistry.
Synthesis, characterization and DNA interaction studies …
Research in the Chenoweth laboratory is grounded in organic chemistry and molecular recognition with applications to biological and materials problems. We synthesize molecules and study their properties and interactions for a broad range of applications in bioorganic and materials chemistry. We are particularly interested in the design and synthesis of new molecules that can modulate nucleic acid and protein structure. Additionally, we are equally interested in the synthesis of new materials with sensing and self-assembly properties.
Facile Synthesis of Electroactive and ..
In summary, a new triptycene-based ligand framework has been designed and synthesized. The bis-furan fused triptycene backbone, together with carefully chosen benzoxazole N,O-donor arms, provides a unique pre-organized platform, which can readily bind two irons in the presence of an external carboxylate. There is no significant conformational change in the framework between free ligand L1 and that in the diiron complex, indicating the desired pre-organized character of the ligand platform. Our ongoing research focuses on the investigation of this complex with molecular oxygen as well as further elaboration of the N,O-donor arm to create a hydrophobic pocket for substrate binding. The synthesis of ligand L with a pendent carboxylate on the third wing of the triptycene backbone is also underway.
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