The transformation of chiral signals into macroscopic properties of materials using chirality-responsive polymers
Source abstract
Abstract
The ability to transform the chiral signals of molecules into the macroscopic properties of a material will offer significant advantages in the development of chiral functional devices and chirality-related applications. Chirality-responsive polymers provide an excellent platform to realize this objective, which often involves two basic strategies. The first strategy is to utilize various external stimuli to directly mediate the chiral conformations of a polymer, through which the energy input is transformed into a macroscopic change in the properties of a material. The second strategy is to utilize the enantioselective interaction between polymers and guest chiral molecules to trigger a stepwise conformational change in smart polymers, which then results in transformation of the macroscopic properties. This review summarizes recent progress in generating chirality-responsive polymers based on these strategies and discusses advances in their applications as chiral sensors, liquid crystals, optical and electrical devices, nanomachines and so on. We then introduce the emerging field of chiral bio-interface materials, in which chiral signals are transformed into changes in the macroscopic behavior of cells and biomacromolecules based on the stereo-specific interactions between biological systems and artificial materials. Chirality – the ‘handedness’ of entities whose mirror images of each other are not superimposable, such as our left and right hands, or helices that twist in opposite directions – is a crucial concept in chemistry and biology: changing the handedness of chiral molecules has a profound impact on their properties. Guangyan Qing and Taolei Sun review how chiral-responsive polymers can convey a signal from the molecular to the macroscopic level. Two strategies can be adopted: incorporating chiral units into the structure of stimuli-responsive polymers, or altering interactions between polymers and chiral molecules. Specific triggers, such as chemical or thermal signals, alter the chirality of these systems, which in turn affect their macromolecular and materials properties. This can be exploited to construct functional devices, such as for sensing or electronic applications, and to control the conformation of inherently chiral biosystems. Life is a multiscale chiral system, which ingeneously combine small chiral biomolecules to biomacromolecules with special stereo-conformations and functions via chemical bonding and weak chemical interactions, for example, hydrogen bonding and hydrophobic interactions, which further assemble to build up macroscopic biological entities showing distinct assymetric characteristics, for example, right-handed conches and so on. This brings much inspiration to construct artificial systems being able to transform chiral signals to macroscopic properties of materials based on chirality-responsive polymers, which find broad applications in various domains of chemical engineering, industry, biology and medicine.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Synthesis and Properties of Aromatic Compounds · Supramolecular Self-Assembly in Materials · Molecular spectroscopy and chirality
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (88)
Show source-provided references
1. Berthod, A. Chiral recognition mechanisms. Anal. Chem. 78, 2093 (2006).10.1021/ac0693823 ↗
2. Hazen, R. M. & Sholl, D. S. Chiral selection on inorganic crystalline surfaces. Nat. Mater. 2, 367 (2003).10.1038/nmat879 ↗
3. Fasel, R., Parschau, M. & Ernst, K. H. Amplification of chirality in two-dimensional enantiomorphous lattices. Nature 439, 449 (2006).10.1038/nature04419 ↗
4. Berg, J. M., Tymoczko, J. L. & Stryer, L. Biochemistry (5th Ed.) (W. H. Freeman: New York, USA, 2002).
5. Grande, C. & Patel, N. H. Nodal signalling is involved in left–right asymmetry in snails. Nature 457, 1007 (2009).10.1038/nature07603 ↗
6. Jesson, L. K. & Barrett, S. C. H. Enantiostyly: solving the puzzle of mirror-image flowers. Nature 417, 707 (2002).10.1038/417707a ↗
7. Friedman, L. & Miller, J. G. Odor incongruity and chirality. Science 172, 1044 (1971).10.1126/science.172.3987.1044 ↗
8. Hanein, D., Geiger, B. & Addadi, L. Differential adhesion of cells to enantiomorphous crystal surfaces. Science 263, 1413 (1994).10.1126/science.8128221 ↗
9. O’Neill, M. & Kelly, S. M. Liquid crystals for charge transport, luminescence, and photonics. Adv. Mater. 15, 1135 (2003).10.1002/adma.200300009 ↗
10. Zheludev, N. I. The road ahead for metamaterials. Science 328, 582 (2010).10.1126/science.1186756 ↗
11. Taylor, M. S. & Jacobsen, E. N. Asymmetric catalysis by chiral hydrogen-bond donors. Angew. Chem. Int. Ed. 45, 1520 (2006).10.1002/anie.200503132 ↗
12. Pu, L. Fluorescence of organic molecules in chiral recognition. Chem. Rev. 104, 1687 (2004).10.1021/cr030052h ↗
13. Maier, N. M., Franco, P. & Lindner, W. Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A. 906, 3 (2001).10.1016/S0021-9673(00)00532-X ↗
14. Lendlein, A. & Shastri, V. P. Stimuli-sensitive polymers. Adv. Mater. 22, 3344 (2010).10.1002/adma.201002520 ↗
15. Stuart, M. A. C., Huck, W. T. S., Genzer, J., Müller, M., Ober, C., Stamm, M., Sukhorukov, G. B., Szleifer, I., Tsukruk, V. V., Urban, M., Winnik, F., Zauscher, S., Luzinov, I. & Minko, S. Emerging applications of stimuli-responsive polymer materials. Nat. Mater. 9, 101 (2010).10.1038/nmat2614 ↗
16. Sun, T. & Qing, G. Biomimetic smart interface materials for biological applications. Adv. Mater. 23, H57 (2011).10.1002/adma.201004326 ↗
17. Yashima, E., Maeda, K., Iida, H., Furusho, Y. & Nagai, K. Helical polymers: synthesis, structures, and functions. Chem. Rev. 109, 6102 (2009).10.1021/cr900162q ↗
18. Nel, A. E., Mädler, L., Velegol, D., Xia, T., Hoek, E. M. V., Somasundaran, P., Klaessig, F., Castranova, V. & Thompson, M. Understanding biophysicochemical interactions at the nano–bio interface. Nat. Mater. 8, 543 (2009).10.1038/nmat2442 ↗
19. Zhang, M. X., Qing, G. Y. & Sun, T. L. Chiral biointerface materials. Chem. Soc. Rev. doi: 10.1039/C1CS15209B (2012).10.1039/C1CS15209B ↗
20. Liu, F. & Urban, M. W. Recent advances and challenges in designing stimuli-responsive polymers. Prog. Polym. Sci. 35, 3 (2010).10.1016/j.progpolymsci.2009.10.002 ↗
21. Tang, K., Green, M. M., Cheon, K. S., Selinger, J. V. & Garetz, B. A. Chiral conflict. The effect of temperature on the helical sense of a polymer controlled by the competition between structurally different enantiomers: from dilute solution to the lyotropic liquid crystal state. J. Am. Chem. Soc. 125, 7313 (2003).10.1021/ja030065c ↗
22. Sakai, R., Otsuka, I., Satoh, T., Kakuchi, R., Kaga, H. & Kakuchi, T. Thermoresponsive on-off switching of chiroptical property induced in poly(4′-ethynylbenzo-15-crown-5)/α-amino acid system. Macromolecules 39, 4032 (2006).10.1021/ma060376i ↗
23. Miyagawa, T., Furuko, A., Maeda, K., Katagiri, H., Furusho, Y. & Yashima, E. Dual memory of enantiomeric helices in a polyacetylene induced by a single enantiomer. J. Am. Chem. Soc. 127, 5018 (2005).10.1021/ja0509634 ↗
24. Kim, H. J., Lee, E., Park, H. S. & Lee, M. Dynamic extension-contraction motion in supramolecular springs. J. Am. Chem. Soc. 129, 10994 (2007).10.1021/ja073554b ↗
25. Shiraki, T., Dawn, A., Tsuchiya, Y. & Shinkai, S. Thermo- and solvent-responsive polymer complex created from supramolecular complexation between a helix-forming polysaccharide and a cationic polythiophene. J. Am. Chem. Soc. 132, 13928 (2010).10.1021/ja1067349 ↗
26. Tang, H. Z., Novak, B. M., He, J. T. & Polavarapu, P. L. A thermal and solvocontrollable cylindrical nanoshutter based on a single screw-sense helical polyguanidine. Angew. Chem. Int. Ed. 44, 7298 (2005).10.1002/anie.200501977 ↗
27. Percec, V., Rudick, J. G., Peterca, M. & Heiney, P. A. Nanomechanical function from self-organizable dendronized helical polyphenylacetylenes. J. Am. Chem. Soc. 130, 7503 (2008).10.1021/ja801863e ↗
28. Kajitani, T., Okoshi, K., Sakurai, S. I., Kumaki, J. & Yashima, E. Helix-sense controlled polymerization of a single phenyl isocyanide enantiomer leading to diastereomeric helical polyisocyanides with opposite helix-sense and cholesteric liquid crystals with opposite twist-sense. J. Am. Chem. Soc. 128, 708 (2006).10.1021/ja0576536 ↗
29. Onouchi, H., Okoshi, K., Kajitani, T., Sakurai, S. I., Nagai, K., Kumaki, J., Onitsuka, K. & Yashima, E. Two- and three-dimensional smectic ordering of single-handed helical polymers. J. Am. Chem. Soc. 130, 229 (2008).10.1021/ja074627u ↗
30. Sakurai, S. I., Okoshi, K., Kumaki, J. & Yashima, E. Two-dimensional surface chirality control by solvent-induced helicity inversion of a helical polyacetylene on graphite. J. Am. Chem. Soc. 128, 5650 (2006).10.1021/ja061238b ↗
31. Zhao, H. C., Sanda, F. & Masuda, T. Transformation of helical sense of poly(N-propargylamides) controlled by competition between structurally different enantiomeric amino acids. Macromolecules 37, 8888 (2004).10.1021/ma048834f ↗
32. Yang, C. T., Wang, Y. L. & Chang, Y. C. Effect of solvents and temperature on the conformation of poly(β-benzyl-l-aspartate) brushes. Biomacromolecules 11, 1308 (2010).10.1021/bm1000907 ↗
33. Sanji, T., Kato, N. & Tanaka, M. Switching of optical activity in oligosilane through pH-responsive chiral wrapping with amylose. Macromolecules 39, 7508 (2006).10.1021/ma061791d ↗
34. Duan, P. F., Qin, L., Zhu, X. F. & Liu, M. H. Hierarchical self-assembly of amphiphilic peptide dendrons: Evolution of diverse chiral nanostructures through hydrogel formation over a wide pH range. Chem. Eur. J. 17, 6389 (2011).10.1002/chem.201003049 ↗
35. Lien le, T. N., Shiraki, T., Dawn, A., Tsuchiya, Y., Tokunaga, D., Tamaru, S., Enomoto, N., Hojo, J. & Shinkai, S. A pH-responsive carboxylic β-1,3-glucan polysaccharide for complexation with polymeric guests. Org. Biomol. Chem. 9, 4266 (2011).10.1039/c1ob05114h ↗
36. Cho, J. I., Tanaka, M., Sato, S., Kinbara, K. & Aida, T. Oligo(4-aminopiperidine-4-carboxylic acid): an unusual basic oligopeptide with an acid-induced helical conformation. J. Am. Chem. Soc. 132, 13176 (2010).10.1021/ja106118w ↗
37. Pijper, D., Jongejan, M. G. M., Meetsmia, A. & Feringa, B. L. Light-controlled supramolecular helicity of a liquid crystalline phase using a helical polymer functionalized with a single chiroptical molecular switch. J. Am. Chem. Soc. 130, 4541 (2008).10.1021/ja711283c ↗
38. Zhao, H. C., Sanda, F. & Masuda, T. Stimuli-responsive conjugated polymers. Synthesis and chiroptical properties of polyacetylene carrying L-glutamic acid and Azobenzene in the side chain. Polymer 47, 2596 (2006).10.1016/j.polymer.2006.02.022 ↗
39. Ouchi, Y., Morisaki, Y., Ogoshi, T. & Chujo, Y. Synthesis of a stimuli-responsive P-chiral polymer with chiral phosphorus atoms and azobenzene moieties in the main chain. Chem. Asian J. 2, 397 (2007).10.1002/asia.200600378 ↗
40. Choi, S. -W., Kawauchi, S., Ha, N. Y. & Takezoe, H. Photoinduced chirality in azobenzene-containing polymer systems. Phys. Chem. Chem. Phys. 9, 3671 (2007).10.1039/b702835k ↗
41. Zheng, Z., Su, Z., Wang, L., Xua, J., Zhang, Q. & Yang, J. Photoinduced chirality in achiral liquid crystalline azobenzene polymers containing different polar side groups. Euro. Polym. J. 43, 2738 (2007).10.1016/j.eurpolymj.2007.01.055 ↗
42. Tejedor, R. M., Oriol, L., Serrano, J. L., Ureña, F. P. & González, J. J. L. Photoinduced chiral nematic organization in an achiral glassy nematic azopolymer. Adv. Funct. Mater. 17, 3486 (2007).10.1002/adfm.200700202 ↗
43. Pan, X., Jiang, H., Wang, Y., Lei, Z., Zou, G., Zhang, Q. & Wang, K. Supramolecular chirality formation of bisazobenzene-substituted polydiacetylene LB films. J. Colloid Interface Sci. 354, 880 (2011).10.1016/j.jcis.2010.11.059 ↗
44. Satrijo, A., Meskers, S. C. J. & Swager, T. M. Probing a conjugated polymer's transfer of organization-dependent properties from solutions to films. J. Am. Chem. Soc. 128, 9030 (2006).10.1021/ja063027c ↗
45. Deng, J., Zhou, C., Chen, C., Song, N. H. & Su, Z. X. Synthesis and redox-driven chiroptically switching properties of viologen-containing optically active polymer with main-chain axial chirality. Macromolecules 41, 7805 (2008).10.1021/ma8014646 ↗
46. Deng, J., Zhou, C. & Song, N. H. Chiroptically active photonics polymers: synthesis and chiroptically switching properties of helical polyacetylene bearing electrochromic viologens in the side chains. Macromolecules 42, 6865 (2009).10.1021/ma901326h ↗
47. Ohta, E., Sato, H., Ando, S., Kosaka, A., Fukushima, T., Hashizume, D., Yamasaki, M., Hasegawa, K., Muraoka, A., Ushiyama, H., Yamashita, K. & Aida, T. Redox-responsive molecular helices with highly condensed π-clouds. Nat. Chem. 3, 68 (2011).10.1038/nchem.900 ↗
48. Sakurai, S. I., Okoshi, K., Kumaki, J. & Yashima, E. Two-dimensional hierarchical self-assembly of one-handed helical polymers on graphite. Angew. Chem. Int. Ed. 45, 1245 (2006).10.1002/anie.200503136 ↗
49. Kumaki, J., Kawauchi, T., Okoshi, K., Kusanagi, H. & Yashima, F. Supramolecular helical structure of the stereocomplex composed of complementary isotactic and syndiotactic poly(methyl methacrylate)s as revealed by atomic force microscopy. Angew. Chem. Int. Ed. 46, 5348 (2007).10.1002/anie.200700455 ↗
50. Cheuk, K. K. L., Li, B. S., Lam, J. W. Y., Xie, Y. & Tang, B. Z. Synthesis, chain helicity, assembling structure, and biological compatibility of poly(phenylacetylene)s containing l-alanine moieties. Macromolecules 41, 5997 (2008).10.1021/ma800976e ↗
51. Goh, M., Kyotani, M. & Akagi, K. Highly twisted helical polyacetylene with morphology free from the bundle of fibrils synthesized in chiral nematic liquid crystal reaction field. J. Am. Chem. Soc. 129, 8519 (2007).10.1021/ja070701x ↗
52. Huang, J., Egan, V. M., Guo, H., Yoon, J. Y., Briseno, A. L., Rauda, I. E., Garrell, R. L., Knobler, C. M., Zhou, F. & Kaner, R. B. Enantioselective discrimination of D- and L-phenylalanine by chiral polyaniline thin films. Adv. Mater. 15, 1158 (2003).10.1002/adma.200304835 ↗
53. Yan, Y., Yu, Z., Huang, Y. W., Yuan, W. X. & Wei, Z. X. Helical polyaniline nanofibers induced by chiral dopants by a polymerization process. Adv. Mater. 19, 3353 (2007).10.1002/adma.200700846 ↗
54. Nagai, K., Sakajiri, K., Maeda, K., Okoshi, K., Sato, T. & Yashima, E. Hierarchical amplification of macromolecular helicity in a lyotropic liquid crystalline charged poly(phenylacetylene) by nonracemic dopants in water and its helical structure. Macromolecules 39, 5371 (2006).10.1021/ma0606760 ↗
55. Goto, H., Furusho, Y. & Yashima, E. Double helical oligoresorcinols specifically recognize oligosaccharides via heteroduplex formation through noncovalent interactions in water. J. Am. Chem. Soc. 129, 9168 (2007).10.1021/ja0730359 ↗
56. Wu, Z. Q., Nagai, K., Banno, M., Okoshi, K., Onitsuka, K. & Yashima, E. Enantiomer-selective and helix-sense-selective living block copolymerization of isocyanide enantiomers initiated by single-handed helical poly(phenyl isocyanide)s. J. Am. Chem. Soc. 131, 6708 (2009).10.1021/ja900036n ↗
57. Onouchi, H., Okoshi, K., Kajitani, T., Sakurai, S. I., Nagai, K., Kumaki, J., Onitsuka, K. & Yashima, E. Two- and three-dimensional smectic ordering of single-handed helical polymers. J. Am. Chem. Soc. 130, 229 (2008).10.1021/ja074627u ↗
58. Nishimura, T., Tsuchiya, K., Ohsawa, S., Maeda, K., Yashima, E., Nakamura, Y. & Nishimura, J. Macromolecular helicity induction on a poly(phenylacetylene) with C2-symmetric chiral [60]fullerene-bisadducts. J. Am. Chem. Soc. 126, 11711 (2004).10.1021/ja046633l ↗
59. Kawauchi, T., Kumaki, J., Kitaura, A., Okoshi, K., Kusanagi, H., Kobayashi, K., Sugai, T., Shinohara, H. & Yashima, E. Encapsulation of fullerenes in a helical PMMA cavity leading to a robust processable complex with a macromolecular helicity memory. Angew. Chem. Int. Ed. 47, 515 (2008).10.1002/anie.200703655 ↗
60. Miyagawa, T., Yamamoto, M., Muraki, R., Onouchi, H. & Yashima, E. Supramolecular helical assembly of an achiral cyanine dye in an induced helical amphiphilic poly(phenylacetylene) interior in water. J. Am. Chem. Soc. 129, 3676 (2007).10.1021/ja068951l ↗
61. Onouchi, H., Miyagawa, T., Morino, K. & Yashima, E. Assisted formation of chiral porphyrin homoaggregates by an induced helical poly(phenylacetylene) template and their chiral memory. Angew. Chem. Int. Ed. 45, 2381 (2006).10.1002/anie.200504162 ↗
62. Nishimura, T., Takatani, K., Sakurai, S. I., Maeda, K. & Yashima, E. A helical array of pendant fullerenes on an optically active polyphenylacetylene. Angew. Chem. Int. Ed. 41, 3602 (2002).10.1002/1521-3773(20021004)41:19<3602::AID-ANIE3602>3.0.CO;2-4 ↗
63. Ohsawa, S., Maeda, K. & Yashima, E. Syntheses and chiroptical properties of optically active helical poly(phenylacetylene)s bearing [60]fullerene pendants. Macromolecules 40, 9244 (2007).10.1021/ma7022342 ↗
64. Nishimura, T., Ohsawa, S., Maeda, K. & Yashima, E. A helical array of pendant fullerenes on a helical poly(phenylacetylene) induced by non-covalent chiral interactions. Chem. Commun. 646 (2004).10.1039/b312511d ↗
65. Nonokawa, R. & Yashima, E. Detection and amplification of a small enantiomeric imbalance in α-amino acids by a helical poly(phenylacetylene) with crown ether pendants. J. Am. Chem. Soc. 125, 1278 (2003).10.1021/ja028348c ↗
66. de Witte, P. A. J., Castriciano, M., Cornelissen, J. J. L. M., Scolaro, L. M., Nolte, R. J. M. & Rowan, A. E. Helical polymer-anchored porphyrin nanorods. Chem. Eur. J. 9, 1775 (2003).10.1002/chem.200390204 ↗
67. Maeda, K., Mochizuki, H., Watanabe, M. & Yashima, E. Switching of macromolecular helicity of optically active poly(phenylacetylene)s bearing cyclodextrin pendants induced by various external stimuli. J. Am. Chem. Soc. 128, 7639 (2006).10.1021/ja060858+ ↗
68. Smith, D. K. Lost in translation? Chirality effects in the self-assembly of nanostructured gel-phase materials. Chem. Soc. Rev. 38, 684 (2009).10.1039/b800409a ↗
69. Goto, H., Zhang, H. Q. & Yashima, E. Chiral stimuli-responsive gels: Helicity induction in poly(phenylacetylene) gels bearing a carboxyl group with chiral amines. J. Am. Chem. Soc. 125, 2516 (2003).10.1021/ja029036c ↗
70. Hirst, A. R., Smith, D. K., Feiters, M. C. & Geurts, H. P. M. Two component dendritic gel: effect of stereochemistry on the on the supramolecular chiral assembly. Chem. Eur. J. 10, 5901 (2004).10.1002/chem.200400502 ↗
71. Hirst, A. R., Huang, B. Q., Castelletto, V., Hamley, I. W. & Smith, D. K. Self-organisation in the assembly of gels from mixtures of different dendritic peptide building blocks. Chem. Eur. J. 13, 2180 (2007).10.1002/chem.200601665 ↗
72. Morino, K., Oobo, M. & Yashima, E. Helicity induction in a poly(phenylacetylene) bearing Aza-18-crown-6 ether pendants with optically active bis(amino acid)s and its chiral stimuli-responsive gelation. Macromolecules 38, 3461 (2005).10.1021/ma047303o ↗
73. Patra, T., Pal, A. & Dey, J. Smart supramolecular hydrogel of Nα-(4-n-Alkyloxybenzoyl)-l-histidine exhibiting pH-modulated properties. Langmuir 26, 7761 (2010).10.1021/la904540x ↗
74. Luo, Z. L., Wang, S. K. & Zhang, S. G. Fabrication of self-assembling d-form peptide nanofiber scaffold d-EAK16 for rapid hemostasis. Biomaterials 32, 2013 (2011).10.1016/j.biomaterials.2010.11.049 ↗
75. Yao, X., Song, Y. L. & Jiang, L. Applications of bio-inspired special wettable surfaces. Adv. Mater. 23, 719 (2011).10.1002/adma.201002689 ↗
76. Qing, G. & Sun, T. Chirality-triggered wettability switching on a smart polymer surface. Adv. Mater. 23, 1615 (2011).10.1002/adma.201004082 ↗
77. Tomar, S., Green, M. M. & Day, L. A. DNA-protein interactions as the source of large-length-scale chirality evident in the liquid crystal behavior of filamentous bacteriophages. J. Am. Chem. Soc. 129, 3367 (2007).10.1021/ja068498d ↗
78. Barry, E., Beller, D. & Dogic, Z. A model liquid crystalline system based on rodlike viruses with variable chirality and persistence length. Soft Matter 5, 2563 (2009).
79. Chung, W. J., Oh, J. W., Kwak, K., Lee, B. Y., Meyer, J., Wang, E., Hexemer, A. & Lee, S. W. Biomimetic self-templating supramolecular structures. Nature 478, 364 (2011).10.1038/nature10513 ↗
80. Geva, M., Frolow, F., Eisenstein, M. & Addadi, L. Antibody recognition of chiral surfaces. enantiomorphous crystals of leucine-leucine-tyrosine. J. Am. Chem. Soc. 125, 696 (2003).10.1021/ja027942j ↗
81. Geva, M., Eisenstein, M. & Addadi, L. Antibody recognition of chiral surfaces. Structural models of antibody complexes with leucine–leucine–tyrosine crystal surfaces. Proteins 55, 862 (2004).10.1002/prot.20042 ↗
82. Sun, T., Han, D., Riehemann, K., Chi, L. & Fuchs, H. Stereospecific interaction between immune cells and chiral surfaces. J. Am. Chem. Soc. 129, 1496 (2007).10.1021/ja0686155 ↗
83. Tang, K., Gan, H., Li, Y., Chi, L., Sun, T. & Fuchs, H. Stereoselective interaction between DNA and chiral surfaces. J. Am. Chem. Soc. 130, 11284 (2008).10.1021/ja8044184 ↗
84. Gan, H., Tang, K., Sun, T., Hirtz, M., Li, Y., Chi, L., Butz, S. & Fuchs, H. Selective adsorption of DNA on chiral surfaces: supercoiled or relaxed conformation. Angew. Chem. Int. Ed. 48, 5282 (2009).10.1002/anie.200806295 ↗
85. Li, Y., Zhou, Y., Wang, H. Y., Perrett, S., Zhao, Y., Tang, Z. & Nie, G. Chirality of glutathione surface coating affects the cytotoxicity of quantum dots. Angew. Chem. Int. Ed. 50, 5860 (2011).10.1002/anie.201008206 ↗
86. Wang, X., Gan, H., Sun, T., Su, B., Fuchs, H., Vestweber, D. & Butz, S. Stereochemistry triggered differential cell behaviours on chiral polymer surfaces. Soft Matter 6, 3851 (2010).10.1039/c0sm00151a ↗
87. Wang, X., Gan, H. & Sun, T. Chiral design for polymeric biointerface: the influence of surface chirality on protein adsorption. Adv. Funct. Mater. 21, 3276 (2011).10.1002/adfm.201101032 ↗
88. Yi, Q., Wen, X., Li, L., He, B., Nie, Y., Wu, Y., Zhang, Z. & Gu, Z. The chiral effects on the responses of osteoblastic cells to the polymeric substrates. Euro. Polym. J. 45, 1970 (2009).10.1016/j.eurpolymj.2009.04.018 ↗