Responsive Supramolecular Polymers Based on the Bis[alkynylplatinum(II)] Terpyridine Molecular Tweezer/Arene Recognition Motif

Tian, Yu-Kui; Shi, Yong; Yang, Zhi-Shuai; Wang, Feng

doi:10.1002/anie.201402192

Cited by 150 publications

(60 citation statements)

References 40 publications

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“…198,199 Wang and coworkers reported supramolecular polymers by incorporating this tweezer−guest molecular recognition ( Figure 32). 200 They designed heteroditopic AB-type monomers 54, which consisted of a tweezer group and a pyrene group on each side. Supramolecular polymers formed through the tweezer−pyrene complexation (K ≈ 10 4 M −1 ) on the basis of a ring−chain equilibrium mechanism.…”

Section: Aromatic Donor−acceptor Interactionsmentioning

confidence: 99%

Supramolecular Polymers: Historical Development, Preparation, Characterization, and Functions

et al. 2015

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Section: Aromatic Donor−acceptor Interactionsmentioning

confidence: 99%

Supramolecular Polymers: Historical Development, Preparation, Characterization, and Functions

et al. 2015

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“…Of course, a variety of molecular clips and molecular tweezer architectures have been studied over the years [21] most notably by the groups of Nolte, [2] Zimmerman, [22,23] and Klaerner. [24,25] For example, Zimmerman studied molecular tweezers that feature acridine walls held apart by a dibenzoacridine spacer and demonstrated their ability to recognize electron poor aromatic guests including nucleotides in organic solvent.…”

Section: Introductionmentioning

confidence: 99%

Glycoluril‐Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water

She

Moncelet

Gilberg

et al. 2016

Chemistry A European J

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Molecular clip 1 remains monomeric in water and engages in host•guest recognition processes with suitable guests. We report the Ka values for 32 1•guest complexes measured by 1H NMR, UV/Vis, and fluorescence titrations. The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests which distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests. Electrostatic effects play a dominant role in the recognition process whereby ion-dipole interactions may occur between ammonium ions and the C=O groups of 1, between the SO3− groups of 1 and pendant cationic groups on the guest, and within the cavity of 1 by cation-π interactions. Host 1 displays high affinity toward dicationic guests with large planar aromatic surfaces (e.g. naphthalene diimide NDI+ and perylene diimide PDI+) and cationic dyes derived from acridine (e.g. methylene blue and azure A). The critical importance of cation-π interactions was ascertained by a comparison of analogous neutral and cationic guests (e.g. methylene violet vs. methylene blue; quinoline vs. N-methylquinolinium; acridine vs. N-methylacridinium; neutral red vs. neutral red H+) whose affinities differ by up to 380-fold. We demonstrate that the high affinity of 1 toward methylene blue (Ka = 3.92 × 107 M−1; Kd = 25 nM) allows for the selective sequestration and destaining of U87 cells stained with methylene blue.

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“…[2] Because of its high association constant( K ass = 6 10 7 m À1 in CHCl 3 )a nd easy synthetic accessibility,t he quadruple hydrogen-bonding unit of the ureidopyrimidinone (UPy) moiety is one of the most commonly used building blocksi na ssembling supramolecular polymers. [2][3][4] Molecules containing two UPy moieties often form long linear supramolecular polymerc hains,e ither by isodesmic or ringchain polymerization mechanisms, as studied thoroughly by Meijer and others. [2][3][4] Molecules containing two UPy moieties often form long linear supramolecular polymerc hains,e ither by isodesmic or ringchain polymerization mechanisms, as studied thoroughly by Meijer and others.…”

Section: Introductionmentioning

confidence: 99%

A Phosphorescent Platinum(II) Bipyridyl Supramolecular Polymer Based on Quadruple Hydrogen Bonds

Liu

Niu

Chen

et al. 2016

Chemistry A European J

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A platinum(II) bipyridyl complex bearing bis-ureidopyrimidinone (Pt-bisUPy) has been designed and its self-assembling behavior has been thoroughly investigated by H NMR, DOSY NMR, Ubbelohde viscometry analysis, UV/Vis, and emission spectroscopies. Pt-bisUPy underwent concentration-dependent ring-chain polymerization in apolar solvents. Hydrogen-bonding interactions play an important role during the formation of the supramolecular polymers. Hydrogen-bonded supramolecular polymers were transformed to nanoparticles in water through the miniemulsion method. These nanoparticles showed strong π-π excimeric emission. Metal-metal-to-ligand charge transfer (MMLCT) from Pt-Pt interactions was not significant in the emission spectrum. The phosphorescence of the nanoparticle persisted even under aerobic conditions. The triplet state of these phosphorescent nanomaterials were long-lived and possessed moderate emission quantum yields. Furthermore, the low toxicity of these materials promises a place for them in in vitro and in vivo bioimaging.

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Responsive Supramolecular Polymers Based on the Bis[alkynylplatinum(II)] Terpyridine Molecular Tweezer/Arene Recognition Motif

Cited by 150 publications

References 40 publications

Supramolecular Polymers: Historical Development, Preparation, Characterization, and Functions

Supramolecular Polymers: Historical Development, Preparation, Characterization, and Functions

Glycoluril‐Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water

A Phosphorescent Platinum(II) Bipyridyl Supramolecular Polymer Based on Quadruple Hydrogen Bonds

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