Synthesis and characterization of polyisocyanides derived from alanine and glycine dipeptides

Cornelissen, Jeroen J. L. M.; Graswinckel, W.S.; Adams, P. J.; Nachtegaal, G.H.; Kentgens, A.P.M.; Sommerdijk, Nico A. J. M.; Nolte, Roeland J. M.

doi:10.1002/pola.10083

Cited by 59 publications

(64 citation statements)

References 23 publications

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“…Such behavior in AFM observations is consistent with the results of previously reported polyisocyanides. 17,29 In addition, dynamic structure of poly-3a was observed by FS-AFM (Supplementary Movie S1).…”

Section: Resultsmentioning

confidence: 91%

Synthesis of polyisocyanides bearing oligothiophene pendants: higher-order structural control through pendant framework design

Ikai

Takagi

Shinohara

et al. 2015

Polym J

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L-Alanine-based polyisocyanides bearing oligothiophene (OT) pendants (poly-3a and poly-3b) were synthesized and the influence of the OT pendants on the chiroptical properties and helix-forming abilities of the polymers was investigated. Poly-3a bearing a quinquethiophene unit with two n-hexyl chains successfully formed a preferred-handed helical conformation by simultaneous interactions of the OT-pendant π-π stacking and hydrogen bonding of the amide groups. In contrast, poly-3b, which possesses a branched alkyl chain on behalf of the terminal n-hexyl chain of poly-3a, did not form a higher-ordered helical conformation. The results suggest that the structure of the alkyl chains positioned far from the polymer backbones remotely and sensitively affected the ability of the polymer to form a helical conformation. We also found that the structure of the OT pendants significantly affect the molecular weight as observed by AFM measurements. The polyisocyanide poly-3c bearing a bithiophene unit was additionally synthesized to examine the influence of the number of thiophene rings within the OT pendants on the higher-order structure formation.

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Section: Resultsmentioning

confidence: 91%

Synthesis of polyisocyanides bearing oligothiophene pendants: higher-order structural control through pendant framework design

Ikai

Takagi

Shinohara

et al. 2015

Polym J

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“…The circular dichroism spectrum of 2 in CHCl 3 shows Cotton effects in the absorption region of perylene, as well as for the imine groups of the polyisocyanide backbone 12. The latter Cotton effect is observed for polyisocyanides with alanine dipeptide sidegroups that form hydrogen‐bonding arrays along the polymer 13. This provides us with a clear signature indicating that polymer 2 has a rigid helical backbone, which is stabilized through a hydrogen‐bonding network between the amino acid side chains, as shown schematically in Figure 1 b.…”

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confidence: 73%

Investigation of Perylene Photonic Wires by Combined Single‐Molecule Fluorescence and Atomic Force Microscopy

et al. 2004

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Heterogeneous optical behavior of perylene polyisocyanides, which arises from different structures of the polymer backbone, is revealed by the combination of single‐molecule fluorescence spectroscopy and atomic force microscopy. Short nonhelical perylene oligomers exhibit monomer‐like fluorescence properties, whereas long helical perylene fiber emission arises from excimer sites after delocalization of the excitation along the polymer backbone (see picture).

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“…Studies involving main‐chain and dendronized PICs have shown that the chain length and backbone design affect thermal properties and crystallinity, although some side‐chain functionalized PICs have reported no melting or glass transition in the range of 20–200 °C . As we were more interested in the design of block copolymers showcasing the heterogeneity of polymerization techniques used, we investigated whether the compatibilization of a coil or sheet‐type bcp affects the properties of the PIC.…”

Section: Resultsmentioning

confidence: 99%

Coil‐helix and sheet‐helix block copolymers via macroinitiation from telechelic ROMP polymers

Elacqua

Croom

Lye

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Coil-helix and sheet-helix block copolymers are synthesized by combining the ring-opening metathesis polymerization (ROMP) of norbornene or paracyclophanediene with the anionic polymerization of phenyl isocyanide. Key to the design is the use of an l-ethynyl palladium (II) functionalized chaintransfer agent (CTA) that can be exploited in a stepwise manner for the termination of ROMP and the initiation of the anionic polymerization. Both the coil-and sheet-macroinitiators, and the ensuing covalent block copolymers, are analyzed using 1 H NMR spectroscopy and gel-permeation chromatography. In all cases, the Pd-end group is maintained and all polymers demonstrate a monomodal distribution with dispersities ( -D) of 1.1-1.4. The resulting helix-coil and helix-sheet block copolymers formed by the macroinitiation route still demonstrate their intrinsic properties (fluorescence, preferential helixsense).

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Synthesis and characterization of polyisocyanides derived from alanine and glycine dipeptides

Cited by 59 publications

References 23 publications

Synthesis of polyisocyanides bearing oligothiophene pendants: higher-order structural control through pendant framework design

Synthesis of polyisocyanides bearing oligothiophene pendants: higher-order structural control through pendant framework design

Investigation of Perylene Photonic Wires by Combined Single‐Molecule Fluorescence and Atomic Force Microscopy

Coil‐helix and sheet‐helix block copolymers via macroinitiation from telechelic ROMP polymers

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