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Cite This: Chem. Mater. 2018, 30, 2074−2083
Different Origins of Strain-Induced Chirality Inversion of Co2+Triggered Supramolecular Peptide Polymers Hyesong Park,†,§ Ka Young Kim,†,§ Sung Ho Jung,† Yeonweon Choi,† Hisako Sato,‡ and Jong Hwa Jung*,† †
Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea ‡ Graduate School of Science and Engineering, Department of Chemistry, Ehime University, Matsuyama 790-8577, Japan S Supporting Information *
ABSTRACT: We report a distinctly different dynamic helix inversion pathway of self-assembled terpyridine-based ligands composed of different numbers of peptide moieties with Co2+ and its amplification of strain-induced chirality from an achiral terpyridine moiety. The helical chirality of the metal centers, coordinated by terpyridine ligands, is controlled by strain-induced chirality with complex ligandto-Co2+ ratios. We also show that the distinct helical inversion mechanism is significantly dependent on the number of peptides attached to ligands. The helical inversion pathway of the self-assembled ligand (R-1 and S-1) complexes composed of one alanine analogue (R- or S-2-amino-1-propyl moiety) and one long saturated alkyl chain relies on two steps of chirality with different complex geometries, first from strain-induced chirality originating from an octahedral structure to octahedral structure with different helical direction and then on to helical chirality in a square-pyramidal structure. In contrast, the helix inversion of the selfassembled R-2 and S-2 complexes containing an alanine analogue and two glycine moieties with Co2+ was followed by one step to form two distinct coexisting complex geometries having the same helical direction. In particular, the circular dichroism (CD) intensities of the self-assembled R-1 and R-2 complexes with Co2+ were 900−1500-fold amplified compared to those of free R-1 and R-2. The Gibbs free energies of the self-assembled complexes with different geometries were also calculated by temperaturedependent CD observation; the square-pyramidal structure of the self-assembled R-1 complex with Co2+ was more stable than the self-assembled R-2 complex with Co2+. Furthermore, the self-assembled R-1 and S-1 complexes with 1.0 equiv of Co2+ could classify amino acids by their chirality. dialkylpolysilanes27 as well as the temperature-induced helicity inversions of switchable polyacetylenes,28−32 polydiarylsilanes,33 and polyisocyanates,34−36 among others.37−44 In particular, a variety of specific noncovalent interactions have been used to build such assemblies.45−49 Among them, metal-bound self-assemblies are the most extensively used strategy for constructing supramolecular architectures with chiral geometries.50−60 In most previous examples, these systems have relied on the presence of chiral ligands to bias the handedness of the dynamic metal complexes. Yashima and co-workers50 demonstrated remote-controlled dynamic chirality of metal centers coordinated by 2,2-bispyridine ligands bearing dynamic helical oligopeptides. In addition, Miyake et al. 21,41,51−53 demonstrated that a peptide-based ligand composed of a chiral hexacoordinated metal center and two achiral pentapeptide chains with a Co2+ ion dynamically converted a left-handed M cis-α structure to a right-handed P cis-α one upon addition of an NO3− anion with a change in coordination geometry by one step. We also reported that the
1. INTRODUCTION Control of helicity in dynamic supramolecular assemblies is an attractive challenge with implications for our understanding of functional biological helicity as well as for the possible development of novel chiral materials that could be useful in the production and separation of enantiomers. Furthermore, the supramolecular assemblies of which helicity can be controlled have a great potential to be extended to the development of useful chiral materials such as sensors,1−3 catalysts,4−6 switches,7,8 and memory devices9 with specific functionalities that involve chiral recognition and sensing, asymmetric catalysis, and chiral optoelectronic properties.10,11 The well-known right-handed double-helical structure representative of B-form DNA, for instance, can undergo inversion to generate the left-handed Z-form DNA helix by exposure to high-salt environments, chemical modification, or complexation with cations and other chemicals.12−20 While the diversity of synthetic systems adopting helical conformations is extensive,21−24 investigations showing controlled transformation between different helical senses are surprisingly rare. Existing synthetic systems known to undergo helical switching as a result of changes in their environment include the solventdependent inversion of helical metal complexes25,26 and © 2018 American Chemical Society
Received: January 5, 2018 Revised: March 7, 2018 Published: March 7, 2018 2074
DOI: 10.1021/acs.chemmater.8b00057 Chem. Mater. 2018, 30, 2074−2083
Article
Chemistry of Materials helicity of terpyridine-based ligands containing one alanine analogue moiety and one cis-double-bond-bridged long alkyl chain complex with Co2+ could be controlled upon addition of Co2+.61 More interestingly, microscopic observation in the gel state showed that both the left-handed M and the right-handed P of terpyridine-based ligand complexes with Co2+ coexisted in the range of 0.2−0.8 equiv of Co2+. Such mono- and oligopeptide groups have been used as chiral cores to transfer helicity to an achiral moiety at the molecular level and/or self-assembled supramolecules.62,63 Thus, the helicity of the self-assembled supramolecular complexes was mainly controlled by the stereoenantiomer of the peptide and/or complex geometry such as octahedral and square-pyramidal structures. Here, we report a distinctly different dynamic helical inversion mechanism of self-assembled terpyridine-based ligands composed of different numbers of peptide moieties in the presence of Co2+ and its dramatic enhancement of straininduced chirality from an achiral terpyridine moiety. When the chirality-switchable metal complex was combined with an alanine analogue and/or glycine moieties, the dynamic inversion of the strain-induced chirality of the self-assembled R-1 and S-1 complexes with Co2+ occurred in two steps: through octahedral, to octahedral with a different helical direction, to square-pyramidal structures.64,65 In contrast, the helix inversion of the self-assembled R-2 and S-2 complexes containing an alanine analogue and two glycine moieties with Co2+ occurred in one step with two distinct coexisting complex geometries having the same helical direction. To the best of our knowledge, these observations constitute the first observation of dynamic chirality inversion by a distinctly different pathway, which strongly depended upon the number of peptides. The dramatically enhanced helicity of the self-assembled complexes also originated from the strain-induced chirality of the achiral terpyridine moieties of the complex formation with Co2+ and not from the stereoenantiomeric alanine analogue.
2.2. Helicity Inversion of the Self-Assembled R-1 and S-1 Complexes. To determine the chiroptical response, we observed CD spectra of the self-assembled R-1 and S-1 complexes with Co(NO3)2 in THF. The CD spectrum of the self-assembled R-1 without Co2+ exhibited a weak positive signal at 285 nm, and the signal intensity gradually increased up to 0.5 equiv of Co2+ with taking the form of one symmetrical band with no shoulder, indicating one complex structure with right-handed (P) helicity (Figure 1A).21,41,51−53,61 The CD
2. RESULTS AND DISCUSSION 2.1. UV−Vis Study of Self-Assembled Complexes with Co2+. The absorption spectra of R-1 in tetrahydrofuran (THF) are shown in Figure S1A. Without Co2+, compound R-1 exhibited two absorption bands at 275 nm (ε275 = 3.02 × 104 M−1 cm−1) with a shoulder at 310 nm (ε310 = 4.62 × 103 M−1 cm−1), which was ascribed to the π−π* and n−π* transitions. The addition of Co2+ to the solution of R-1 in THF significantly changed the absorption spectra (Figure S1 in Supporting Information), increasing the intensity of bands at 310 and 320 nm. In particular, the absorption band at 320 nm was newly generated upon addition of Co2+, and this originated from metal−ligand charge transfer (MLCT) between Co2+ and the terpyridine moieties of R-1.66−69 The absorption band at 310 nm showed two-step slope changes at approximately 0.5 and 1.0 equiv of Co2+ (Figure S1B) that were ascribed to the high concentration of R-1. These results indicate that the selfassembled R-1 formed 1:2 (Co2+/R-1) and 1:1 complexes with Co2+ in THF. We also observed the d−d transition−absorption band of the self-assembled R-1 complexes with 0.5 and 1.0 equiv of Co2+. As shown in Figure S1C and E, the absorption band of the self-assembled R-1 in the presence of a Co2+ equivalent of 0.083 mM Lphenylalanine was added, whereas it was not changed upon addition of D-phenylalanine (Figures 6C and S19B). The helicity inversion of the self-assembled R-1 complex with 1.0 equiv of Co2+ upon addition of D-phenylalanine was also evidenced by the microscopic analysis. The SEM images clearly exhibited the morphological change from left-handed (M) helicity to right-handed (P) helicity upon addition of 0.166 mM D-phenylalanine (Figure S20). We further evaluated the sensing behavior of the self-assembled R-1 and S-1 complexes with 1.0 equiv of Co2+ on several classes of amino acids including valine, serine, leucine, histidine, alanine, and arginine. All of the tested amino acids exhibited classifiability by their chirality with the self-assembled R-1 and S-1 complexes. The negative CD signal of the self-assembled R-1 with 1 equiv of Co2+ was inverted upon addition of D-form amino acids with similar intensities; however, it was not changed with L-form amino acids (Figure S21). With the self-assembled S-1 complex with 1 equiv of Co2+, L-form amino acids were sensitive, showing exactly opposite tendencies. To investigate the influence of the amino acids on the helicity of the self-assembled complexes, we measured IR spectra of the self-assembled complexes of R-1 and S-1 with 1.0 equiv of Co2+ in the absence and the presence of amino acids. As shown in Figure S22A, CO bands of amide group in Dphenylalanine (1696 cm−1) and that in the self-assembled R-1 with 1.0 equiv of Co2+ (1645 cm−1) were shifted to a lower wavenumber and to a higher wavenumber, respectively, when D-phenylalanine was added to the self-assembled R-1 complex, indicating that the hydrogen-bonding interaction was formed between the amide group in R-1 and that in D-phenylalanine. In contrast, any shift was not shown upon addition of Lphenylalanine, implying the absence of the intermolecular interaction between the self-assembled R-1 complex and L-
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ASSOCIATED CONTENT
* Supporting Information S
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.chemmater.8b00057. Experimental section, CD spectra, UV−vis spectra, ESI mass spectra, and SEM photograph data (PDF) 2080
DOI: 10.1021/acs.chemmater.8b00057 Chem. Mater. 2018, 30, 2074−2083
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Chemistry of Materials
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Hisako Sato: 0000-0002-3927-1794 Jong Hwa Jung: 0000-0002-8936-2272 Author Contributions §
H.P. and K.Y.K. contributed equally.
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS This work was supported by the NRF (2015R1A2A2A05001400, 2018R1A2B2003637, and 2017R1A4A1014595) supported by the Ministry of Education, Science and Technology, Korea. In addition, this work was partially supported by a grant from the Next-Generation BioGreen 21 Program (SSAC, Grant no. PJ013186052018), Rural Development Administration, Korea.
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DOI: 10.1021/acs.chemmater.8b00057 Chem. Mater. 2018, 30, 2074−2083
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DOI: 10.1021/acs.chemmater.8b00057 Chem. Mater. 2018, 30, 2074−2083
