Photonenergy‐Controlled Symmetry Breaking with Circularly Polarized Light
Abstract
Circularly polarized light (CPL) is known to be a true chiral entity capable of generating absolute molecular asymmetry. However, the degree of inducible optical activity depends on the λ of the incident CPL. Exposure of amorphous films of rac-alanine to tunable CPL led to enantiomeric excesses (ee) which not only follow the helicity but also the energy of driving electromagnetic radiation. Postirradiation analyses using enantioselective multidimensional GC revealed energy-controlled ee values of up to 4.2 %, which correlate with theoretical predictions based on newly recorded anisotropy spectra g(λ). The tunability of asymmetric photochemical induction implies that both magnitude and sign can be fully controlled by CPL. Such stereocontrol provides novel insights into the wavelength and polarization dependence of asymmetric photochemical reactions and are highly relevant for absolute asymmetric molecular synthesis and for understanding the origins of homochirality in living matter.
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Solid-state VUV-CPL irradiation of leucine and alanine has achieved e.e. values of 5.2 ± 0.5% and 4.2 ± 0.2%, respectively.
“More recently, the same team improved the selectivity of the photolysis process, thanks to amorphous samples of finelytuned thickness, providing e.e. values of 5.2 Æ 0.5% and 4.2 Æ 0.2% for leucine, 197 and alanine, 198,199 respectively.”
From Possible chemical and physical scenarios towards biological homochirality (2022) · cites this paper as [198]
Exposure of circularly polarized light (CPL) in simulated interstellar media can induce a mirror symmetry breaking between the formation of L- or D-alanine, and the imbalance depended on the wavelength of the incident CPL and the sense of its rotation.
“Meierhenrich and co-workers, among others, showed that the exposure of circularly polarized light (CPL) in simulated interstellar media can induce a mirror symmetry breaking between the formation of L- or D- alanine. Besides, the imbalance depended on the wavelength of the incident CPL and the sense of its rotation.(Garcia et al., 2019; Meinert et al., 2014)”
From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Meinert et al., 2014
Chiral C3 sugar derivative glyceric acid was found as racemic mixtures, consistent with an abiotic origin.
“Chiral C3 sugar derivative, glyceric acid, was found as racemic mixtures, which is consistent with an abiotic origin. (Garcia et al., 2019; Meinert et al., 2014; Myrgorodska et al., 2015)”
From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Meinert et al., 2014
Cites
Anisotropy Spectra of Amino Acids
Meinert, C., Bredehöft, J. H., Filippi, J., Baraud, Y., Nahon, L., Wien, F., Jones, N. C., Hoffmann, S. V., & Meierhenrich, U. J. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108997 · Cited by 64 · see citing works
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The Search for Chiral Asymmetry as a Potential Biosignature in our Solar System
Glavin, D. P., Burton, A. S., Elsila, J. E., Aponte, J. C., & Dworkin, J. P. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00474 · Cited by 293 · see citing works
Possible chemical and physical scenarios towards biological homochirality
Sallembien, Q., Bouteiller, L., Crassous, J., & Raynal, M. (2022) · Chemical Society Reviews · doi:10.1039/d1cs01179k · Cited by 186 · see citing works
Myrgorodska, I., Meinert, C., Martins, Z., Le Sergeant d'Hendecourt, L., & Meierhenrich, U. J. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201409354 · Cited by 68 · see citing works
Self-citationThe Astrophysical Formation of Asymmetric Molecules and the Emergence of a Chiral Bias
Garcia, A. D., Meinert, C., Sugahara, H., Jones, N. C., Hoffmann, S. V., & Meierhenrich, U. J. (2019) · Life · doi:10.3390/life9010029 · Cited by 47 · see citing works
Self-citationSymmetry Breaking in Self-Assembled Nanoassemblies
Sang, Y., & Liu, M. (2019) · Symmetry · doi:10.3390/sym11080950 · Cited by 35 · see citing works
“However, due to the small anisotropy factors (<10−3), the obtained enantiomeric excess in most cases of asymmetric photolysis and photosynthesis is undesirable (<4%) [142,143].”
BackgroundThe Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments
Chieffo, C., Shvetsova, A., Skorda, F., Lopez, A., & Fiore, M. (2023) · Astrobiology · doi:10.1089/ast.2023.0007 · Cited by 21 · see citing works
- Authors
- Meinert, C., Hoffmann, S. V., Cassam‐Chenaï, P., Evans, A. C., Giri, C., Nahon, L., & Meierhenrich, U. J.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Aarhus University (DK)
- Max Planck Society (DE)
- Corresponding author
- Meinert, Cornelia
- Nahon, Laurent
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2013-11-13
- Volume
- 53
- Issue
- 1
- Pages
- 210-214
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2116658086
- Cited by
- 121
- References
- 1
- Citations by year
- 2026: 2 · 2025: 10 · 2024: 12 · 2023: 6 · 2022: 6 · 2021: 14 · 2020: 14 · 2019: 10 · 2018: 8 · 2017: 7 · 2016: 9 · 2015: 9 · 2014: 14
- FWCI
- 4.78
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Max Planck Digital Library (submittedVersion)
- MPG.PuRe (Max Planck Society) (submittedVersion)
- Funders
- Agence Nationale de la Recherche (ANR-07-BLAN-0293, ANR-12-IS07-0006)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Physical Sciences › Materials Science › Materials Chemistry › Photochromic and Fluorescence Chemistry
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Keywords
- circularly polarized light, chiral induction, optical activity, enantiomeric excess, wavelength dependence, absolute asymmetric synthesis, homochirality, amorphous films
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