Single Crystal to Single Crystal Polymerization of a Self-Assembled Diacetylene Macrocycle Affords Columnar Polydiacetylenes

Xu, Weiming; Smith, Mark D.; Krause, Jeanette A.; Greytak, Andrew B.; Ma, Shuguo; Read, Cory M.; Shimizu, Linda S.

doi:10.1021/cg401380a

Cited by 54 publications

(40 citation statements)

References 95 publications

(132 reference statements)

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“…The diyne systems are parallel as requested; nevertheless, the angle of the reactive carbons and mostly their distance separations are not favorable, being distorted and much too long, respectively (Figure 4). Topochemical polymerization of diacetylene is also prevented because there is no long range parallel stacking of diynes [58][59][60][61][62][63][64][65][66][67]. …”

Section: Crystallographic Studiesmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH 2 -diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H¨¨¨O=C) or halogen bond interactions (diyne-Br¨¨¨O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions.

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Section: Crystallographic Studiesmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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“…Stabilities of the polymers were verified by thermogravimetric analysis (TGA) . For this purpose, polymer of 2 was subjected to TGA under inert argon atmosphere between 27 and 500 °C, at a heating rate of 10 °C min −1 .…”

Section: Resultsmentioning

confidence: 99%

Multicolor Reversible Thermochromic Properties of Gallic Acid-Cored Polydiacetylenes Appended with Poly(alkyl aryl ether) Dendrons

Singh

Jayaraman

2016

Macromol. Chem. Phys.

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This study describes synthesis of zero and fi rst generation poly(alkyl aryl ether) dendrons onto a gallic acid core, tethered with three diacetylene moieties and their photopolymerization. Resulting polydiacetylenes are studied by (i) UV-vis, IR, Raman spectroscopies, and chromoisomerism by naked eye visualization; (ii) their stabilities by differential scanning calorimetry, thermogravimetric method, and (iii) structure, morphology, and emission behavior by scanning electron, transmission electron, atomic force microscopies, powder X-ray diffraction method, and fl uorescence spectroscopy. The dendron-appended polydiacetylenes show robust nanoribbon morphologies and exhibit multicolor, reversible chromoisomerism at temperatures up to 300 °C. Reversibility of amide bond IR frequencies, as a function of temperature, shows the polymer stabilities, in addition to the results of thermal and powder X-ray diffraction studies. Temperature annealed polymers having red color phase exhibit emission maxima at 572 and 633 nm, that shift to higher wavelength upon heating and revert to the initial emission wavelengths on cooling.

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“…Hollow tubular nanostructures offer a variety of applications in chemistry, biochemistry and materials science as specific molecular reaction vessels [41], screening activities of membrane channels and the nanoscale fluidic transport systems [42]. However, highly stable and programmable organic nanotubes (ONT) are very rare [43,44].…”

Section: Peptoid-based Crystalline Nanotubementioning

confidence: 99%

Peptoid-based hierarchically-structured biomimetic nanomaterials: Synthesis, characterization and applications

et al. 2020

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Peptoids (or poly-N-substituted glycines) are a promising class of bioinspired sequence-defined polymers due to their highly efficient synthesis, high chemical stability, enzyme hydrolysis resistance, and biocompatibility. By tuning the side chain chemistry of peptoids, it allows for precise control over sequences and achieving a large side-chain diversity. Due to these unique features, in the last several years, many amphiphilic peptoids were designed as highly tunable building blocks for the preparation of biomimetic nanomaterials with well-defined hierarchical structures and desired functionalities. Herein, we provide an overview of the recent achievements in this area by dividing them into the following three aspects. First, mica-and silica-templated peptoid selfassembly are summarized. The presence of inorganic substrates provides the guarantee of investigating their selfassembly mechanisms and interactions between peptoids and substrates using nanoscale characterization techniques, particularly in situ atomic force microscopy (AFM) and AFMbased dynamic force spectroscopy (AFM-DFS). Second, solution-phase self-assembly of peptoids into nanotubes and nanosheets is presented, as well as their self-repair properties. Third, the applications of peptoid-based nanomaterials are outlined, including the construction of catalytic nanomaterials as a template and cytosolic delivery as cargoes.

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Single Crystal to Single Crystal Polymerization of a Self-Assembled Diacetylene Macrocycle Affords Columnar Polydiacetylenes

Cited by 54 publications

References 95 publications

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

Multicolor Reversible Thermochromic Properties of Gallic Acid-Cored Polydiacetylenes Appended with Poly(alkyl aryl ether) Dendrons

Peptoid-based hierarchically-structured biomimetic nanomaterials: Synthesis, characterization and applications

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