An efficient one-pot route to an aza-bridged bis-phenanthroline macrocyclic compound

Wang, Wen-Jwu; Chuang, Kuo-Shen; Luo, Chi-Fong; Liu, Haiyang

doi:10.1016/s0040-4039(00)01525-2

“…Research Articles elucidated using FT-IR, XPS,UV-vis,and 13 CNMR spectroscopies.T he powder XRD and HR-TEM analyses of the ABBPM-COF combined with structural simulations revealed its crystallinity to have an ABC stacking mode.T his COF material showed good chemical stability in hash conditions, including 9Maqueous KOHand concentrated HCl solutions. Moreover,t he insulating ABBPM-COF pellet had an electrical conductivity of 2.6 10 À4 S/cm at room temperature after being exposed to iodine vapor.…”

Section: Angewandte Chemiementioning

confidence: 99%

Catalyst‐ and Solvent‐Free Synthesis of a Chemically Stable Aza‐Bridged Bis(phenanthroline) Macrocycle‐Linked Covalent Organic Framework

Jiang

¹

,

Jung

²

,

Joo

³

et al. 2021

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Developing new linkage-based covalent organic frameworks (COFs) is one of the major topics in reticular chemistry.E lectrically conductive COFs have enabled applications in energy storage and electrochemical catalysis,w hich are not feasible using insulating COFs.D espite significant advances,t he construction of chemically stable conductive COFs by the formation of new linkages remains relatively unexplored and challenging. Here we report the solvent-and catalyst-free synthesis of at wo-dimensional aza-bridged bis(phenanthroline) macrocycle-linked COF (ABBPM-COF) from the thermally induced poly-condensation of at ri-topic monomer and ammonia gas.The ABBPM-COF structure was elucidated using multiple techniques,i ncluding X-rayd iffraction analysis combined with structural simulation, revealing its crystalline nature with an ABC stackingmode.Further experiments demonstrated its excellent chemical stability in acid/base solutions.E lectrical-conductivity measurements showed that the insulating ABBPM-COF becomes as emiconducting material after exposure to iodine vapor.

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“…Arylboron compounds are very useful building blocks in organic chemistry [17,18,19,20,21,22]; the most commonly used method to form the C–B bond is iridium-catalyzed C–H borylation [23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38]. The well-known catalyst system for this transformation is the combination of an iridium catalyst and a 2,2’-bipyridine-type ligand, such as 4,4′-di-tert-butyl bipyridine (dtbpy), 1,10-phenanthroline (1,10-phen), or 3,4,7,8-tetramethyl-1,10-phenanthroline (tmphen) [39,40,41,42]. Previous studies demonstrated that Compound A shown in Scheme 2 was the key intermediate in the iridium-catalyzed C–H borylation reaction.…”

Section: Resultsmentioning

confidence: 99%

NNB-Type Tridentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C–H Borylation

Ding

¹

,

Wang

²

,

Miao

³

et al. 2019

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Boryl ligands play a very important role in catalysis because of their very high electron-donating property. In this paper, NNB-type boryl anions were designed as tridentate ligands to promote aryl C–H borylation. In combination with [IrCl(COD)]2, they generate a highly active catalyst for a broad range of (hetero)arene substrates, including highly electron-rich and/or sterically hindered ones. This work provides a new NNB-type tridentate boryl ligand to support homogeneous organometallic catalysis.

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“…Forschungsartikel elucidated using FT-IR, XPS,UV-vis,and 13 CNMR spectroscopies.T he powder XRD and HR-TEM analyses of the ABBPM-COF combined with structural simulations revealed its crystallinity to have an ABC stacking mode.T his COF material showed good chemical stability in hash conditions, including 9Maqueous KOHand concentrated HCl solutions. Moreover,t he insulating ABBPM-COF pellet had an electrical conductivity of 2.6 10 À4 S/cm at room temperature after being exposed to iodine vapor.…”

Section: Angewandte Chemiementioning

confidence: 99%

Catalyst‐ and Solvent‐Free Synthesis of a Chemically Stable Aza‐Bridged Bis(phenanthroline) Macrocycle‐Linked Covalent Organic Framework

Jiang

¹

,

Jung

²

,

Joo

³

et al. 2021

Angewandte Chemie

4

0

View full text Add to dashboard Cite

Developing new linkage-based covalent organic frameworks (COFs) is one of the major topics in reticular chemistry.E lectrically conductive COFs have enabled applications in energy storage and electrochemical catalysis,w hich are not feasible using insulating COFs.D espite significant advances,t he construction of chemically stable conductive COFs by the formation of new linkages remains relatively unexplored and challenging. Here we report the solvent-and catalyst-free synthesis of at wo-dimensional aza-bridged bis(phenanthroline) macrocycle-linked COF (ABBPM-COF) from the thermally induced poly-condensation of at ri-topic monomer and ammonia gas.The ABBPM-COF structure was elucidated using multiple techniques,i ncluding X-rayd iffraction analysis combined with structural simulation, revealing its crystalline nature with an ABC stackingmode.Further experiments demonstrated its excellent chemical stability in acid/base solutions.E lectrical-conductivity measurements showed that the insulating ABBPM-COF becomes as emiconducting material after exposure to iodine vapor.

show abstract

An efficient one-pot route to an aza-bridged bis-phenanthroline macrocyclic compound

Cited by 22 publications

References 16 publications

Catalyst‐ and Solvent‐Free Synthesis of a Chemically Stable Aza‐Bridged Bis(phenanthroline) Macrocycle‐Linked Covalent Organic Framework

Catalyst‐ and Solvent‐Free Synthesis of a Chemically Stable Aza‐Bridged Bis(phenanthroline) Macrocycle‐Linked Covalent Organic Framework

NNB-Type Tridentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C–H Borylation

Catalyst‐ and Solvent‐Free Synthesis of a Chemically Stable Aza‐Bridged Bis(phenanthroline) Macrocycle‐Linked Covalent Organic Framework

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