Chiral Graphene Quantum Dots

Suzuki, Nozomu; Wang, Yichun; Elvati, Paolo; Qu, Zhi-Bei; Kim, Kyoungwon; Jiang, Shuang; Baumeister, Elizabeth; Lee, Jaewook; Yeom, Bongjun; Bahng, Joong Hwan; Lee, Jaebeom; Violi, Angela; Kotov, Nicholas A.

doi:10.1021/acsnano.5b06369

Title: Chiral Graphene Quantum Dots

Journal Article · Fri Jan 15 00:00:00 EST 2016 · ACS Nano

DOI:https://doi.org/10.1021/acsnano.5b06369· OSTI ID:1435721

Suzuki, Nozomu ^[1]; Wang, Yichun ^[2]; Elvati, Paolo ^[3]; Qu, Zhi-Bei ^[4]; Kim, Kyoungwon ^[5]; Jiang, Shuang ^[4]; Baumeister, Elizabeth ^[6]; Lee, Jaewook ^[7]; Yeom, Bongjun ^[5]; Bahng, Joong Hwan ^[2]; Lee, Jaebeom ^[8]; Violi, Angela ^[9]; Kotov, Nicholas A. ^[10]

Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemical Engineering; Univ. of Michigan, Ann Arbor, MI (United States). Biointerfaces Inst.; Nara Inst. of Science and Technology, Ikoma, Nara (Japan)
Univ. of Michigan, Ann Arbor, MI (United States). Biointerfaces Inst.; Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Biomedical Engineering
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Biomedical Engineering; Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Mechanical Engineering
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemical Engineering
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemical Engineering; Univ. of Michigan, Ann Arbor, MI (United States). Biointerfaces Inst.
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Mechanical Engineering
Univ. of Michigan, Ann Arbor, MI (United States). Biointerfaces Inst.; Pusan National Univ., Miryang (Korea, Republic of). Dept. of Cogno-Mechatronics Engineering
Pusan National Univ., Miryang (Korea, Republic of). Dept. of Cogno-Mechatronics Engineering
Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Biomedical Engineering; Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Mechanical Engineering; Univ. of Michigan, Ann Arbor, MI (United States). Dept.of Macromolecular Science and Engineering, Biophysics Program
Univ. of Michigan, Ann Arbor, MI (United States). Biointerfaces Inst., Dept. of Biomedical Engineering, Dept. of Mechanical Engineering, and Dept. of Materials Science and Engineering

Chiral nanostructures from metals and semiconductors attract wide interest as components for polarization-enabled optoelectronic devices. Similarly to other fields of nanotechnology, graphene-based materials can greatly enrich physical and chemical phenomena associated with optical and electronic properties of chiral nanostructures and facilitate their applications in biology as well as other areas. Here, we report that covalent attachment of l/d-cysteine moieties to the edges of graphene quantum dots (GQDs) leads to their helical buckling due to chiral interactions at the “crowded” edges. Circular dichroism (CD) spectra of the GQDs revealed bands at ca. 210–220 and 250–265 nm that changed their signs for different chirality of the cysteine edge ligands. The high-energy chiroptical peaks at 210–220 nm correspond to the hybridized molecular orbitals involving the chiral center of amino acids and atoms of graphene edges. Diverse experimental and modeling data, including density functional theory calculations of CD spectra with probabilistic distribution of GQD isomers, indicate that the band at 250–265 nm originates from the three-dimensional twisting of the graphene sheet and can be attributed to the chiral excitonic transitions. The positive and negative low-energy CD bands correspond to the left and right helicity of GQDs, respectively. Exposure of liver HepG2 cells to l/d-GQDs reveals their general biocompatibility and a noticeable difference in the toxicity of the stereoisomers. Molecular dynamics simulations demonstrated that d-GQDs have a stronger tendency to accumulate within the cellular membrane than l-GQDs. Finally, emergence of nanoscale chirality in GQDs decorated with biomolecules is expected to be a general stereochemical phenomenon for flexible sheets of nanomaterials.

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Research Organization:: Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: SC0002619; 2510001; DMR-9871177

OSTI ID:: 1435721

Journal Information:: ACS Nano, Vol. 10, Issue 2; ISSN 1936-0851

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 253 works

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Chiral Carbon Dots Synthesized on Cellulose Nanocrystals Chekini, Mahshid; Prince, Elisabeth; Zhao, Lily Advanced Optical Materials, Vol. 8, Issue 4 https://doi.org/10.1002/adom.201901911	journal	December 2019
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A self-assembled chiral-aptasensor for ATP activity detection Fu, Pan; Sun, Maozhong; Xu, Liguang Nanoscale, Vol. 8, Issue 32 https://doi.org/10.1039/c6nr04086a	journal	January 2016
Transmission of chirality through space and across length scales Morrow, Sarah M.; Bissette, Andrew J.; Fletcher, Stephen P. Nature Nanotechnology, Vol. 12, Issue 5 https://doi.org/10.1038/nnano.2017.62	journal	May 2017
Synthesis of a Helical Bilayer Nanographene Evans, Paul J.; Ouyang, Jiangkun; Favereau, Ludovic Angewandte Chemie, Vol. 130, Issue 23 https://doi.org/10.1002/ange.201800798	journal	March 2018
Colorimetric chiral discrimination of lysine enantiomers and configurable logic gate operation based on fluorescein-functionalized polydiacetylene vesicles Yang, Guang; Ji, Jie; Zhang, Siyu Analytical Methods, Vol. 12, Issue 5 https://doi.org/10.1039/c9ay02518a	journal	January 2020
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Dielectric nanoantennas to manipulate solid-state light emission Bidault, Sébastien; Mivelle, Mathieu; Bonod, Nicolas Journal of Applied Physics, Vol. 126, Issue 9 https://doi.org/10.1063/1.5108641	journal	September 2019
Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral BINOL-functionalized nanoporous graphene oxides Wang, Xu; Guo, Jiahui; Qie, Fengxiang Journal of Materials Science, Vol. 54, Issue 9 https://doi.org/10.1007/s10853-018-03230-9	journal	January 2019
Evolution and Synthesis of Carbon Dots: From Carbon Dots to Carbonized Polymer Dots Xia, Chunlei; Zhu, Shoujun; Feng, Tanglue Advanced Science, Vol. 6, Issue 23 https://doi.org/10.1002/advs.201901316	journal	September 2019
Graphene Quantum Dots Electrochemistry and Sensitive Electrocatalytic Glucose Sensor Development Gupta, Sanju; Smith, Tyler; Banaszak, Alexander Nanomaterials, Vol. 7, Issue 10 https://doi.org/10.3390/nano7100301	journal	September 2017
Design principles of chiral carbon nanodots help convey chirality from molecular to nanoscale level Ðorđević, Luka; Arcudi, Francesca; D’Urso, Alessandro Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05561-2	journal	August 2018
Memristive Devices with Highly Repeatable Analog States Boosted by Graphene Quantum Dots Wang, Changhong; He, Wei; Tong, Yi Small, Vol. 13, Issue 20 https://doi.org/10.1002/smll.201603435	journal	March 2017
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The toxicity of graphene quantum dots Wang, Shujun; Cole, Ivan S.; Li, Qin RSC Advances, Vol. 6, Issue 92 https://doi.org/10.1039/c6ra16516h	journal	January 2016
Unraveling the cooperative synergy of zero-dimensional graphene quantum dots and metal nanocrystals enabled by layer-by-layer assembly Zeng, Zhiping; Xiao, Fang-Xing; Phan, Hung Journal of Materials Chemistry A, Vol. 6, Issue 4 https://doi.org/10.1039/c7ta09119b	journal	January 2018
Chiral Nanoparticle as a New Efficient Antimicrobial Nanoagent Xin, Qi; Liu, Qian; Geng, Lingling Advanced Healthcare Materials, Vol. 6, Issue 4 https://doi.org/10.1002/adhm.201601011	journal	December 2016
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Synthesis of distorted nanographenes containing seven- and eight-membered carbocycles Márquez, Irene R.; Castro-Fernández, Silvia; Millán, Alba Chemical Communications, Vol. 54, Issue 50 https://doi.org/10.1039/c8cc02325e	journal	January 2018
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Predicting the time of entry of nanoparticles in cellular membranes Liu, Changjiang; Elvati, Paolo; Majumder, Sagardip bioRxiv https://doi.org/10.1101/619221	posted_content	April 2019
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Chiral Semiconductor Nanoparticles for Protein Catalysis and Profiling Hao, Changlong; Gao, Rui; Li, Yue Angewandte Chemie International Edition, Vol. 58, Issue 22 https://doi.org/10.1002/anie.201902673	journal	May 2019
Chirality‐Embedded Nanographenes Nishitani, Shohei; Sekiya, Ryo; Haino, Takeharu Angewandte Chemie International Edition, Vol. 59, Issue 2 https://doi.org/10.1002/anie.201910040	journal	January 2020
Tuning the Morphology and Chiroptical Properties of Discrete Gold Nanorods with Amino Acids Zheng, Guangchao; Bao, Zhiyong; Pérez-Juste, Jorge Angewandte Chemie, Vol. 130, Issue 50 https://doi.org/10.1002/ange.201810693	journal	November 2018
Highly Fluorescent Chiral N-S-Doped Carbon Dots from Cysteine: Affecting Cellular Energy Metabolism Li, Feng; Li, Yiye; Yang, Xiao Angewandte Chemie International Edition, Vol. 57, Issue 9 https://doi.org/10.1002/anie.201712453	journal	February 2018
Anti-Biofilm Activity of Graphene Quantum Dots via Self-Assembly with Bacterial Amyloid Proteins Wang, Yichun; Kadiyala, Usha; Qu, Zhibei ACS Nano, Vol. 13, Issue 4 https://doi.org/10.1021/acsnano.8b09403	journal	March 2019
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Boron-mediated sequential alkyne insertion and C–C coupling reactions affording extended π-conjugated molecules Shoji, Yoshiaki; Tanaka, Naoki; Muranaka, Sho Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12704	journal	September 2016

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