Unprecedented Control over Polymerization of <i>n</i>-Hexyl Isocyanate using an Anionic Initiator Having Synchronized Function of Chain-End Protection

Ahn, Jun‐Hwan; Shin, Yeong‐Deuk; Nath, Gaurav; Park, Sang-Yoon; Rahman, M. Shahinur; Samal, Shashadhar; Lee, Jae‐Suk

doi:10.1021/ja0427000

Cited by 69 publications

(85 citation statements)

References 30 publications

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“…We appended a benzamide function onto motor molecule 1 (Figure 2) with the intention that its sodium salt can act as an initiator for the polymerization of ( n )‐hexylisocyanate, yielding poly‐( n )‐hexylisocyanate (PHIC) 15. The resulting polymers are functionalized at the α‐chain‐end with a single enantiomer of a molecular motor (Figure 2).…”

Section: Methodsmentioning

confidence: 99%

Molecular Transmission: Controlling the Twist Sense of a Helical Polymer with a Single Light‐Driven Molecular Motor

Pijper¹,

Feringa²

2007

Angewandte Chemie

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Section: Methodsmentioning

confidence: 99%

Molecular Transmission: Controlling the Twist Sense of a Helical Polymer with a Single Light‐Driven Molecular Motor

Pijper¹,

Feringa²

2007

Angewandte Chemie

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“…It is known that phenyl vinyl sulfoxide [67] and alkyl isocyanate monomers [43][44][45][46] undergo living anionic polymerization to result in interesting polymers, poly(4-phenyl vinyl sulfoxide), convertible to conductive rod-like poly(acetylene) and poly(alkyl isocyanate)s with helical conformation. These specialty functional polymers may also be used, at least to a certain extent, in the linking methodology to synthesize block polymers containing blocks with rod-like and helical conformations.…”

Section: Future Outlookmentioning

confidence: 99%

Precise Synthesis of Block Polymers Composed of Three or More Blocks by Specially Designed Linking Methodologies in Conjunction with Living Anionic Polymerization System

et al. 2013

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This article reviews the successful development of two specially designed linking methodologies in conjunction with a living anionic polymerization system for the synthesis of novel multiblock polymers, composed of three or more blocks, difficult to be synthesized by sequential polymerization. The first methodology with the use of a new heterofunctional linking agent, 2-(4-chloromethylphenyl)ethyldimethylchlorosilane (1), was developed for the synthesis of multiblock polymers containing poly(dimethylsiloxane) (PDMS) blocks. This methodology is based on the selective reaction of the chain-end silanolate anion of living PDMS, with the silyl chloride function of 1, and subsequent linking reaction of the resulting ω-chain-end-benzyl chloride-functionalized polymer with either a living anionic polymer or living anionic block copolymer. With this methodology, various multiblock polymers containing PDMS blocks, up to the pentablock quintopolymer, were successfully synthesized. The second methodology using an α-phenylacrylate (PA) reaction site was developed for the synthesis of multiblock polymers composed of all-vinyl polymer blocks. In this methodology, an α-chain-end-PA-functionalized polymer or block copolymer, via the living anionic polymerization, was first prepared and, then, reacted with appropriate living anionic polymer or block copolymer to link the two polymer chains. As OPEN ACCESSPolymers 2013, 5 1013 a result, ACB (BCA), BAC (CAB), (AB) n , (AC) n , ABA, ACA, BCB, and ABCA multiblock polymers, where A, B, and C were polystyrene, poly(2-vinylpyridine), and poly(methyl methacrylate) segments, could be successfully synthesized. The synthesis of triblock copolymers, BAB, CAC, and CBC, having molecular asymmetry in both side blocks, was also achieved. Furthermore, the use of living anionic polymers, derived from many other monomers, categorized as either of styrene, 2-vinylpyridine, or methyl methacrylate in monomer reactivity, in the linking methodology enabled the number of synthetically possible block polymers to be greatly increased. Once again, all of the block polymers synthesized by these methodologies are new and cannot be synthesized at all by sequential polymerization. They were well-defined in block architecture and precisely controlled in block segment.

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“…17,18 n-Hexyl isocyanate (HIC, 97%, Aldrich, Milwaukee, WI, USA) was dried over CaH 2 and distilled under vacuum. An initiator, sodium benzanilide (Na-BA) in tetrahydrofuran (THF, 50 ml), was prepared from the reaction of equivalent amounts of benzanilide (8.70 g, 0.043 mol) and elemental sodium (1.00 g, 0.043 mol) at room temperature.…”

Section: Materials and Phic Synthesismentioning

confidence: 99%

Reversible conformation-driven order–order transition of peptide-mimic poly(n-alkyl isocyanate) in thin films via selective solvent-annealing

et al. 2012

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We report for the first time the conformational and structural details of peptide-mimic poly(n-hexyl isocyanate) (PHIC). PHIC is a representative poly(n-alkyl isocyanate)s, which have received significant attention because of their unique stiff chain characteristics and potential applications in various fields. A well-ordered hexagonal close packing structure of PHIC with 8 3 helical conformation was clearly observed in the nanoscale thin films that were selectively annealed with carbon disulfide (CS 2 ). A well-ordered multi-bilayer structure of the polymer with b-sheet conformation was also clearly formed in the films that were selectively annealed with toluene. In addition, a fully reversible transformation between these two self-assembled structures was demonstrated by consecutive annealings with CS 2 and toluene.

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Unprecedented Control over Polymerization of n-Hexyl Isocyanate using an Anionic Initiator Having Synchronized Function of Chain-End Protection

Cited by 69 publications

References 30 publications

Molecular Transmission: Controlling the Twist Sense of a Helical Polymer with a Single Light‐Driven Molecular Motor

Molecular Transmission: Controlling the Twist Sense of a Helical Polymer with a Single Light‐Driven Molecular Motor

Precise Synthesis of Block Polymers Composed of Three or More Blocks by Specially Designed Linking Methodologies in Conjunction with Living Anionic Polymerization System

Reversible conformation-driven order–order transition of peptide-mimic poly(n-alkyl isocyanate) in thin films via selective solvent-annealing

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