2,3-Dipyrrolylquinoxaline-Based Anion Sensors

Sessler, Jonathan L.; Andrioletti, Bruno; Anzenbacher, Pavel; Black, Chris; Eller, Leah R.; Furuta, Hiroyuki; Jursíková, Karolina; Maeda, Hiromitsu; Márquez, Manuel; Mizuno, Toshihisa; Try, Andrew C.

doi:10.1007/978-1-4419-8973-4_5

Cited by 5 publications

(3 citation statements)

References 52 publications

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“…Despite the presence of the bulky alkyl groups, the crystal structure revealed “inverted” pyrroles with NH pointing toward the quinoxaline nitrogen atoms (Figure ). Such an inverted conformation was already observed in the solid state for nonalkylated DPQ . The dihedral angle between the two pyrroles was estimated at 17.9°.…”

supporting

confidence: 64%

Facile Preparation of Doubly Dipyrrolylquinoxaline-Bridged Expanded Porphyrins. Synthesis and Structural Characterization of an Unprecedented [20]Tetraphyrin-(2.1.2.1)

2006

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supporting

confidence: 64%

Facile Preparation of Doubly Dipyrrolylquinoxaline-Bridged Expanded Porphyrins. Synthesis and Structural Characterization of an Unprecedented [20]Tetraphyrin-(2.1.2.1)

2006

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“…, respectively. And although DPQ is an electronically neutral acyclic oligopyrrole system, attachment of the electron-withdrawing moiety quinoxaline enhances the polarity of the pyrrole NH, further promoting efficient binding to anions [90,91].…”

Section: Dipyrrolylquinoxalinesmentioning

confidence: 99%

Acyclic Oligopyrrolic Anion Receptors

Maeda

2010

Topics in Heterocyclic Chemistry

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Recent progress in the guest-binding and supramolecular chemistry of anion-responsive acyclic oligopyrroles is summarized here in this chapter. The hydrogen-bonding properties of the pyrrole NH sites determine anion binding in acylic oligopyrroles such as guanidinocarbonyl and amidopyrroles, dipyrrins and their analogs, dipyrrolylquinoxalines, and boron complexes of dipyrrolyldiketones. Linear oligopyrroles can be incorporated as subunits in various macromolecules and complexes by means of covalent and noncovalent interactions; in fact, boron complexes of dipyrrolyldiketones form assembled structures and, with the appropriate substituents, soft materials such as anion-responsive supramolecular gels.

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“…Most of the ligand frameworks used are either rigid or flexible. Ligands having rigid and flexible frameworks with variable coordination sites are relatively uncommon. − The polypyridyl-pyrazine-based 2,3-di(pyridin-2-yl)pyrazino[2,3- f ][1,10] phenanthroline (phpy) ligand offers a rigid framework at the phenanthroline end and flexible donors sites at the pyrazine end. The flexible pyridine donors at the pyrazine end can potentially coordinate with the same/different metals in various coordination modes (Chart ).…”

Section: Introductionmentioning

confidence: 99%

Asymmetrically Coordinated Heterodimetallic Ir–Ru System: Synthesis, Computational, and Anticancer Aspects

et al. 2023

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Herein, we present an unprecedented formation of a heterodinuclear complex [{(ppy)2IrIII}(μ-phpy){RuII(tpy)}](ClO4)2 {[1](ClO4)2} using terpyridyl/phenylpyridine as ancillary ligands and asymmetric phpy as a bridging ligand. The asymmetric binding mode (N∧N-∩-N∧N∧C–) of the phpy ligand in {[1](ClO4)2} is confirmed by 1H, 13C, 1H–1H correlated spectroscopy (COSY), high-resolution mass spectrum (HRMS), single-crystal X-ray crystallography techniques, and solution conductivity measurements. Theoretical investigation suggests that the highest occupied molecular orbital (HOMO) and the least unoccupied molecular orbital (LUMO) of [1]2+ are located on iridium/ppy and phpy, respectively. The complex displays a broad low energy charge transfer (CT) band within 450–575 nm. The time-dependent density functional theory (TDDFT) analysis suggests this as a mixture of metal-to-ligand charge transfer (MLCT) and ligand-to-ligand charge transfer (LLCT), where both ruthenium, iridium, and ligands are involved. Complex {[1](ClO4)2} exhibits RuIIIrIII/RuIIIIrIII- and RuIIIIrIII/RuIIIIrIV-based oxidative couples at 0.83 and 1.39 V, respectively. The complex shows anticancer activity and selectivity toward human breast cancer cells (IC50; MCF-7: 9.3 ± 1.2 μM, and MDA-MB-231: 8.6 ± 1.2 μM) over normal breast cells (MCF 10A: IC50 ≈ 21 ± 1.3 μM). The Western blot analysis and fluorescence microscopy images suggest that combined apoptosis and autophagy are responsible for cancer cell death.

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2,3-Dipyrrolylquinoxaline-Based Anion Sensors

Cited by 5 publications

References 52 publications

Facile Preparation of Doubly Dipyrrolylquinoxaline-Bridged Expanded Porphyrins. Synthesis and Structural Characterization of an Unprecedented [20]Tetraphyrin-(2.1.2.1)

Facile Preparation of Doubly Dipyrrolylquinoxaline-Bridged Expanded Porphyrins. Synthesis and Structural Characterization of an Unprecedented [20]Tetraphyrin-(2.1.2.1)

Acyclic Oligopyrrolic Anion Receptors

Asymmetrically Coordinated Heterodimetallic Ir–Ru System: Synthesis, Computational, and Anticancer Aspects

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