High-dilution synthesis of macrocyclic polycatecholates

Rodgers, S. J.; Ng, Chiu Yuen; Raymond, Kenneth N.

doi:10.1021/ja00299a065

Cited by 43 publications

(18 citation statements)

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“…31 Although the transformation from linear oligomers into cyclic products is thermodynamically favored, the improper chain length and interchain interactions impede the formation of macrocycles, resulting in graphdiyne chain arrays, as illustrated in Figure 6a. On the other hand, when the concentration of (d-BEB-Au) 6 intermediates on surfaces is sufficiently low, that is, appoaching the high-dilution condition, 32 stepwise demetallization of individual (d-BEB-Au) 6 hexagons at mild annealing tempearture could enable the direct conversion to the covalent graphidyne macrocycles (top panel of Figure 6b). For small aggregates of a few (d-BEB-Au) 6 , the templating effect of the Au(111) surface also enhances the formation of macrocycles via merging the closely contacted intermediate rings and intramolecular cyclization (bottom panel of Figure 6b).…”

Section: Resultsmentioning

confidence: 99%

High-Yield Formation of Graphdiyne Macrocycles through On-Surface Assembling and Coupling Reaction

Liu

Zhou

et al. 2018

ACS Nano

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Rationally designed halogenated hydrocarbons are widely used building blocks to fabricate covalent-bonded carbon nanostructures on surfaces through a reaction pathway involving generation and dissociation of organometallic intermediates and irreversible covalent bond formation. Here, we provide a comprehensive picture of the on-surface-assisted homocoupling reaction of 1,3-bis(2-bromoethynyl)benzene on Au(111), aiming for the synthesis of graphdiyne nanostructures. Submolecular resolution scanning tunneling microscopy and noncontact atomic force microscopy observations identify the organometallic intermediates and their self-assemblies formed in the dehalogenation process. The demetallization of the organometallic intermediates at increased temperatures produces butadiyne moieties that spontaneously formed two different covalent structures (i.e., graphdiyne zigzag chains and macrocycles), whose ratio was found to depend on the initial coverage of organometallic intermediates. At the optimal condition, the stepwise demetallization and cyclization led to a high-yield production of graphdiyne macrocycles up to 95%. Statistical analysis and theoretical calculations suggested that the favored formation of macrocycles resulted from the complex interplay between thermodynamic and kinetic processes involving the organometallic bonded intermediates and the covalently bonded butadiyne moieties.

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Section: Resultsmentioning

confidence: 99%

High-Yield Formation of Graphdiyne Macrocycles through On-Surface Assembling and Coupling Reaction

Liu

Zhou

et al. 2018

ACS Nano

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“…348 Finally, Raymond and co-workers reported the hetero macrocyclic enterobactin analogue 507 (Figure 21), showing high affinity for Fe(III). 349 Although most of these compounds have not been investigated for their ability to serve as bacterial xenosiderophores, for DOTRMAHA 499 and TETMAHA 508 growthpromoting effects in the Gram-negative bacteria E. coli, Morganella morganii, and Proteus mirabilis have been demonstrated by Santos and co-workers. 350 Furthermore, investigation with a broad range of E. coli mutants deficient in the biosynthesis of various siderophore outer membrane receptors revealed a high receptor promiscuity for these compounds.…”

Section: Review Synthesismentioning

confidence: 99%

Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis

2022

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Iron is an essential growth factor for bacteria, but although highly abundant in nature, its bioavailability during infection in the human host or the environment is limited. Therefore, bacteria produce and secrete siderophores to ensure their supply with iron. The tris-catecholate siderophore enterobactin and its glycosylated derivatives, the salmochelins, play a crucial role for iron acquisition in several bacteria. As these compounds can serve as carrier molecules for the design of antimicrobial siderophore drug conjugates as well as siderophore-derived tool compounds for the detection of infections with bacteria, their synthesis and the design of artificial analogues is of interest. In this review, we give an overview on the synthesis of enterobactin, biomimetic as well as totally artificial analogues and related drug-conjugates covering up to 12/2021.

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“…The reaction of an aromatic diacid dichloride with a diamine followed by reduction is a common method for producing 1:1, 2:2, 3:3 and higher-order cyclocondensation products. The most detailed study of this type of cyclocondensation reaction was done by Raymond and coworkers for the reactions of terphthalyl dichloride with various diamines as shown in Scheme 4 [14]. Where n = 2, the cyclocondensation products included the trimer (m = 2) (the product of three diacid dichlorides with three diamines) to the hexamer.…”

Section: Nov-dec 2001 1239mentioning

confidence: 99%

“…The yields of pentamer and hexamer products were less than 1%. The best yields were for the dimer (24%), a 28-membered ring, in the reaction using 1,6-diaminohexane (n = 6) and for the trimer (17%), a 30-membered ring, in the reaction with ethylenediamine (n = 2) [14].…”

Section: Nov-dec 2001 1239mentioning

confidence: 99%

One‐step syntheses of macrocyclic compounds: A short review

Krakowiak

Izatt

Bradshaw

2001

Journal of Heterocyclic Chem

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Macrocyclic ligands have been prepared by various one-step cyclooligomerization processes. This short review covers one-step cyclization reactions involving the formation of four to twenty or more new covalent bonds. The new macrocycles reviewed include cyclophanes, biscrown ethers, cryptands, macrolides, cage compounds, calixarenes, homocalixarenes, cucubiturils, and supercryptands all prepared by one-step syntheses.

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High-dilution synthesis of macrocyclic polycatecholates

Cited by 43 publications

References 0 publications

High-Yield Formation of Graphdiyne Macrocycles through On-Surface Assembling and Coupling Reaction

High-Yield Formation of Graphdiyne Macrocycles through On-Surface Assembling and Coupling Reaction

Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis

One‐step syntheses of macrocyclic compounds: A short review

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