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Integration of inherent and induced chirality into subphthalocyanine analogue.

ABSTRACT: Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine skeleton, resulting in a novel type of chiral subphthalocyanine analogue (R/S)-1 of integrated inherent and induced chirality. Impressively, an obviously enhanced optical activity is discerned for (R/S)-1 molecules, and corresponding enhancement mechanism is elucidated in detail. The synthesis strategy based on rational molecular design will open the door towards fabrication of chiral materials with giant optical activity, which will have great potential in chiroptical devices.

SUBMITTER: Zhao L

PROVIDER: S-EPMC4904797 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Integration of inherent and induced chirality into subphthalocyanine analogue.

Zhao Luyang L Qi Dongdong D Wang Kang K Wang Tianyu T Han Bing B Tang Zhiyong Z Jiang Jianzhuang J

Scientific reports 20160613

Conventional conjugated systems are characteristic of only either inherent or induced chirality because of synthetic challenge in combination of chiral segment into the main chromophore. In this work, chiral binaphthyl segment is directly fused into the central chromophore of a subphthalocyanine skeleton, resulting in a novel type of chiral subphthalocyanine analogue (R/S)-1 of integrated inherent and induced chirality. Impressively, an obviously enhanced optical activity is discerned for (R/S)- ...[more]

PMID: 27294871

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Project description:Transfer of chirality, or transmission of asymmetric information from one system to another, plays an essential role in fundamental biological and chemical processes and, therefore, is essential for life. This phenomenon also holds immense potential in spintronics in the context of chirality-induced spin selectivity (CISS). In the CISS, the spatial arrangement of chiral molecules influences the spin state of electrons during the charge-transfer processes. Transfer of chirality from chiral molecules to an achiral material in a hybrid environment enables induction of spin polarization in the achiral material, thus vastly expanding the library of CISS-active electronic materials. Such "induced" CISS signals could have different responses compared to pure chiral molecules because the electronic properties of the achiral material come into play in the former case. In addition, multiple chiral sources can be used, which can have a nontrivial contribution to the induced CISS effect and can act either synergistically or antagonistically. This opens the way to achieving tunability of the CISS signals via chemical means. Earlier, such a chirality-transfer phenomenon and the resulting induced CISS effect were demonstrated in a hybrid system containing carbon nanotubes (CNTs) functionalized with a chiral agent (Fmoc-diphenylalanine l/d). In this context, we extend this result by investigating the role of an additional chiral moiety (l-lysozyme enzyme crystals) in this system. Here, the chiral crystal surrounds the chiral-functionalized CNTs, and we show that synergistic interactions result in more efficient chirality transfer, resulting in nontrivial changes in the CISS effect. This manifests in the form of (a) a stronger CISS signal compared to only one single chiral agent, (b) nonmonotonic temperature dependence and sign reversal of the CISS signal, and (c) persistence of the CISS signal at higher temperatures. Hybrid chiral materials with multiple chiral sources could, therefore, offer intricate control of the CISS signal via modification of its constituents, which is not possible in homogeneous chiral systems with single chiral sources.

Dataset Information

Integration of inherent and induced chirality into subphthalocyanine analogue.

Publications

Integration of inherent and induced chirality into subphthalocyanine analogue.

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