Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Cheng, Hua; Pu, Lin

doi:10.1002/(sici)1521-3935(19990601)200:6<1274::aid-macp1274>3.0.co;2-8

Cited by 25 publications

(6 citation statements)

References 17 publications

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“…The reported chiral conjugated polymers can be divided into two groups: (1) Main chain chiral conjugated polymers, mainly conjugated polymers containing chiral binaphthylene moieties [9][10][11][12][13][14];…”

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confidence: 75%

Designed synthesis and chiroptical properties of regioregular poly(p-phenyleneethynylene-alter-m-phenyleneethynylene) bearing (−)-trans-myrtanoxyl side groups

et al. 2009

Front. Chem. China

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Two regioregular poly(p-phenyleneethynylene-alter-m-phenyleneethynylene)s bearing (-)-transmyrtanoxyl side groups with different substitution patterns were designed and synthesized, e.g. Myr-PMPE-1 and Myr-PMPE-2. In Myr-PMPE-1, the side chiral groups are distributed uniformly along the backbone. In Myr-PMPE-2, the distribution of the side chiral groups is alternatively crowded and loose. Both of these two polymers show no CD signal in solutions because of their good solubility. The investigations of chiroptical properties of these two polymers were carried out in the form of spin-coated films. The films were annealed above the glass temperature of the corresponding polymer, and the effects of annealing temperature and time on the properties of the films were investigated by UV-Vis absorption, fluorescence and circular dichroism spectra. The results show that annealing treatment had no significant effect on the properties of Myr-PMPE-1, including UV-Vis absorption, fluorescence and optical activity. The maximum absolute value of dissymmetry factor (|g max |) was 1.62 Â 10 -4 . On the other hand, annealing treatment significantly affected the properties of Myr-PMPE-2. Without annealing or being annealed below 100°C, Myr-PMPE-2 films show almost no Cotton effect. In contrast, when annealed above 120°C, the absorption and emission of Myr-PMPE-2 films slightly red shifted with increasing annealing temperature and annealing time. Most importantly, the intensity of CD signals increased significantly and the optical activity of Myr-PMPE-2 films markedly increased. After annealing at 140°C for 4 h, the |g max | of Myr-PMPE-2 films was increased up to 3.07 Â 10 -3 , about one order of magnitude higher than that of Myr-PMPE-1 films.

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confidence: 75%

Designed synthesis and chiroptical properties of regioregular poly(p-phenyleneethynylene-alter-m-phenyleneethynylene) bearing (−)-trans-myrtanoxyl side groups

et al. 2009

Front. Chem. China

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“…Several poly(aryleneethynylene)s having chiral binaphthylene moieties in the main chain have been prepared. ,, A propeller-like conformation has been proposed for 118 as one of the possible structures …”

Section: H Poly(aryleneethynylene)smentioning

confidence: 99%

Synthetic Helical Polymers: Conformation and Function

2001

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I. Introduction 4013 II. Helical Polymers 4015 A. Polyolefins 4015 B. Polymethacrylate and Related Polymers 4016 1. Poly(triphenylmethyl methacrylate) 4016 2. Poly(triphenylmethyl methacrylate) Analogues: Anionic Polymerization 4017 3. Poly(triphenylmethyl methacrylate) Analogues: Free-Radical Polymerization 4018 4. Polymers of Other Acrylic Monomers 4022 C. Miscellaneous Vinyl Polymers 4023 D. Polyaldehydes 4023 1. Polychloral and Related Polymers 4023 2. Other Polyaldehydes 4024 E. Polyisocyanides 4024 1. Polymers of Monoisocyanides 4024 2. Polymers of Diisocyanides 4025 F. Polyisocyanates and Related Polymers 4025 1. Polyisocyanates 4025 2. Polycarbodiimides 4027 G. Polyacetylene Derivatives and Related Polymers 4027 1. Polyacetylene Derivatives 4027 2. Polyphosphazene 4029 H. Poly(aryleneethynylene)s 4029 I. Polyarylenes 4030 J. Si-Containing Polymers 4031 1. Polysilanes 4031 2. Polysiloxane 4032 K. Other Types of Polymers 4032 1. Miscellaneous Examples 4032 2. Mimics and Analogues of Biopolymers 4033 III. Helical Polymeric Complexes and Aggregates 4033 A. Helicates 4033 B. Helical Aggregates 4033 IV. Summary and Outlook 4034 V. Acknowledgments 4034 VI. References 4034

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“…We also used 1,1l-binaphthyl-2,2l-diamine ((R)-63) to prepare propeller-like polymers, as amine groups are stronger electron donors than alkoxy groups [22]. Scheme 11.21 shows the conversion of (R)-63 into the desired monomer (R)-66.…”

Section: 1l-binaphthyl-22l-diamine-derived Polymersmentioning

confidence: 95%

Chiral Acetylenic Macromolecules

2004

Acetylene Chemistry

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Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Cited by 25 publications

References 17 publications

Designed synthesis and chiroptical properties of regioregular poly(p-phenyleneethynylene-alter-m-phenyleneethynylene) bearing (−)-trans-myrtanoxyl side groups

Designed synthesis and chiroptical properties of regioregular poly(p-phenyleneethynylene-alter-m-phenyleneethynylene) bearing (−)-trans-myrtanoxyl side groups

Synthetic Helical Polymers: Conformation and Function

Chiral Acetylenic Macromolecules

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