Bipyridinium radical cation dimerization-driven polymeric pleated foldamers and a homoduplex that undergo ion-tuned interconversion

Zhang, Yunchang; Zhang, Dan‐Wei; Wang, Hui; Zhou, Yaming; Li, Zhan‐Ting

doi:10.1039/c5py00419e

Cited by 14 publications

(6 citation statements)

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“…Additionally, given the extended aromatic surface of 1 , the properties of the resulting materials may depend on π-stacking interactions between the conjugated backbones of polymer chains. Such interactions may be promoted by the heteroatom doping present in 1 , as similarly observed in some bipyridinium- or tetrathiafulvalene-containing materials …”

Section: Introductionmentioning

confidence: 70%

Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity

et al. 2020

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Conductive π-conjugated polymers were electrochemically generated from a variety of donor–acceptor pyrroles containing fused perimidine subunits. Alternating oxidative and reductive polarization of these precursors induces multidirectional coupling involving both perimidine and acenaphtho[1,2-c]pyrrole moieties, producing cross-linked polymeric structures. Chemical oxidation experiments and computational analyses of spin densities in the charged pyrrole intermediates indicate that the formation of inter-perimidine linkages occurs prior to pyrrole–pyrrole couplings. In the resulting polymers, a very stable dication state is achievable with the positive charge located on the bis-perimidine linker. These polymers do not show any stable neutral state and can be easily reduced. Cationic and anionic states of these electrogenerated films were investigated in the solid state by UV–vis–NIR and EPR spectroelectrochemistry, assisted by DFT calculations.

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Section: Introductionmentioning

confidence: 70%

Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity

et al. 2020

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“…Hence, 3,6,9,12,15-pentaoxaheptadecanedihydrazide ( 2 ) was prepared. This difunctional PEG can be synthesized from commercially available tetraethylene glycol in two steps according to reported procedures with an overall yield of 47% ( Scheme S4 ) (Wittmann et al., 1998 ; Zhang et al., 2015 ).…”

Section: Resultsmentioning

confidence: 99%

Preparation of a mesoporous silica-based nano-vehicle for dual DOX/CPT pH-triggered delivery

et al. 2018

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A dual doxorubicin/camptothecin (DOX/CPT) pH-triggered drug delivery mesoporous silica nanoparticle (MSN)-based nano-vehicle has been prepared. In this drug-delivery system (DDS), CPT is loaded inside the pores of the MSNs, while DOX is covalently attached to the surface of an aldehyde-functionalized MSN through a dihydrazide–polyethylene glycol chain. Thus, DOX and the linker act as pH-sensitive gatekeeper. The system is versatile and easy to assemble, not requiring the chemical modification of the drugs. While at physiological conditions the release of the drugs is negligible, at acidic pH a burst release of DOX and a gradual release of CPT take place. In vitro cytotoxicity tests have demonstrated that this DDS can deliver efficiently DOX and CPT for combination therapy.

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“…We previously reported that BIPY +• ‐incorporated polymers form pleated sheets in acetonitrile, which is driven by the stacking of the BIPY •+ units . We further prepared water‐soluble polymers P1 ‐ P4 from the condensation reactions of dialdehyde M1 with hydrazine or corresponding acylhydrazine precursors (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Doubly, Triply and Multiply Pleated Sheets of Bipyridinium Radical Cation‐Incorporated Polymers Tuned by Four Cucurbiturils

et al. 2016

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Depending on the size of their cavity, cucurbit[n]urils (CB[n], n=5, 7, 8, and 10) exhibit very different encapsulation selectivity. This feature has been utilized to tune the formation and switching of three kinds of pleated sheets of bipyridinium radical cation (BIPY•+)‐based polymers in water. Driven by the dimerization of the BIPY•+ units, the polymers spontaneously form multiply pleated sheets. These pleated foldamers can be reversibly converted into flexible pseudopoly‐rotaxanes, doubly and triply pleated sheets by CB[7], CB[8] and CB[10], respectively, through selective encapsulation of the macrocycles for one, two or three stacked BIPY•+ units. Adding adamantamonium (ADMT), hexamethylenetetramine (HMTA) or CB[5] to the respective solutions leads to taking away of the CB rings from the polymers due to the formation of more stable 1:1 complexes and as a result, multiply pleated sheets are recovered. UV‐vis absorption spectroscopy has been used to investigate the formation and conversion of the pleated and extended states of the polymers.

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Bipyridinium radical cation dimerization-driven polymeric pleated foldamers and a homoduplex that undergo ion-tuned interconversion

Cited by 14 publications

References 50 publications

Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity

Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity

Preparation of a mesoporous silica-based nano-vehicle for dual DOX/CPT pH-triggered delivery

Doubly, Triply and Multiply Pleated Sheets of Bipyridinium Radical Cation‐Incorporated Polymers Tuned by Four Cucurbiturils

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