Circular dichroism of molecular aggregates: A tutorial.
circular dichroism
supramolecular chirality
Journal
Chirality
ISSN: 1520-636X
Titre abrégé: Chirality
Pays: United States
ID NLM: 8914261
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
revised:
23
02
2023
received:
31
12
2022
accepted:
16
03
2023
medline:
30
3
2023
pubmed:
30
3
2023
entrez:
29
3
2023
Statut:
ppublish
Résumé
In this tutorial, we guide the reader through two alternative approaches to the calculation of circular dichroism (CD) spectra of chiral supramolecular assemblies of non-chiral chromophores. The two seemingly different approaches rely on the same basic approximations and are therefore expected to lead to similar results. For a dimer, we obtain explicit analytic expressions for the CD responses in the two approaches and demonstrate the perfect equivalence of the two methods. Numerical results for larger systems further validate this result. We hope that this tutorial will help young students and scientists entering the field to approach the fascinating topic of supramolecular chirality.
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
681-691Subventions
Organisme : PNRR-MUR
ID : ECS_00000033_ECOSISTER
Organisme : Italian Ministry of University and Research
ID : 2018-2022
Organisme : Italian Ministry of University and Research
ID : 2023-2017
Informations de copyright
© 2023 The Authors. Chirality published by Wiley Periodicals LLC.
Références
Riehl JP, Richardson FS. Circularly polarized luminescence spectroscopy. Chem Rev. 1977;77(6):773-792. doi:10.1021/cr60310a001
Green M, Reidy M, Johnson R, Darling G, O'Leary D, Willson G. Macromolecular stereochemistry: the out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experiment. J am Chem Soc. 1989;111(16):6452-6454. doi:10.1021/ja00198a084
Prins L, Timmerman P, Reinhoudt D. Amplification of chirality: the “sergeants and soldiers” principle applied to dynamic hydrogen-bonded assemblies. J am Chem Soc. 2001;11(123):10153-10163.
Berova N, Di Bari L, Pescitelli G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev. 2007;07(36):914-931.
Berova N, Woody RW, Polavarapu P, Nakanishi K. Comprehensive Chiroptical Spectroscopy: Volume 1 Instrumentation, Methodologies, and Theoretical Simulations. John Wiley Sons; 2012.
Nizar N, Sujith M, Swathi K, Sissa C, Painelli A, Thomas K. Emergent chiroptical properties in supramolecular and plasmonic assemblies. Chem Soc Rev. 2021;09:50.
Koukoulitsa C, Karioti A, Bergonzi M, Pescitelli G, Di Bari L, Skaltsa H. Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece. J Agric Food Chem. 2006;54(15):5388-5392. doi:10.1021/jf061477i
Zhang W, Krohn K, Ding J, et al. Structural and stereochemical studies of α-methylene-γ-lactone-bearing cembrane diterpenoids from a South China Sea soft coral Lobophytum crassum. J Nat Prod. 2008;71(6):961-966. doi:10.1021/np800081p
Hussain H, Akhtar N, Draeger S, et al. New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus Azorica. Eur J Org Chem. 2009;2009(5):749-756. doi:10.1002/ejoc.200801052
Ahmed I, Hussain H, Schulz B, et al. Three new antimicrobial metabolites from the endophytic fungus Phomopsis sp. Eur J Org Chem. 2011;2011(15):2867-2873. doi:10.1002/ejoc.201100158
Mai-Liang, Dong SH, Li HY, Wei WJ, Tu YQ, Gao K. Cytochalasins from Xylaria sp. CFL5, an endophytic fungus of Cephalotaxus fortunei. Nat Prod Bioprospect. 2020;11(1):87-98.
Blaser HU. Chirality and its implications for the pharmaceutical industry. Rendiconti Lincei. 2013;09(24):213-216. doi:10.1007/s12210-012-0220-2
Nguyen L, He H. Chiral drugs: an overview. Int J Biomed Sci. 2006;06(2):85-100.
Abram M, Jakubiec M, Kamiński K. Chirality as an important factor for the development of new antiepileptic drugs. ChemMedChem. 2019;14(20):1744-1761. doi:10.1002/cmdc.201900367
Collina S, Lucarini S, Benet-Buchholz J, Trapp O, Pescitelli G, Berova N. Special issue: chirality in pharmaceutical research and development. Chirality. 2022;34(12):1491-1493. doi:10.1002/chir.23510
Pescitelli G, Bari LD, Berova N. Conformational aspects in the studies of organic compounds by electronic circular dichroism. Chem Soc Rev. 2011;40(9):4603-4625. doi:10.1039/c1cs15036g
Fischer P. Nonlinear optical spectroscopy of chiral molecules. Comprehensive chiroptical spectroscopy. Chirality. 2012;17(8):421-437.
Dubovski N, Shoshan-Galeczki YB, Malach E, Niv MY. Taste and chirality: l-glucose sweetness is mediated by TAS1R2/TAS2R3 receptor. Food Chem. 2022;373(1):131393. doi:10.1016/j.foodchem.2021.131393
Berova N, Nakanishi K, Woody R. Circular Dichroism: Principles and Applications. John Wiley and Sons; 2000:337-395.
Painelli A, Terenziani F, Angiolini L, Benelli T, Giorgini L. Chiral interactions in azobenzene dimers: a combined experimental and theoretical study. Chemistry. 2005;11(20):6053-6063. doi:10.1002/chem.200401081
Pescitelli G. ECD exciton chirality method today: a modern tool for determining absolute configurations. Chirality. 2021;34(2):333-363. doi:10.1002/chir.23393
Lindon J. Encyclopedia of Spectroscopy and Spectrometry. Elsevier; 2010.
Zinna F, Bruhn T, Guido C, et al. Circularly polarized luminescence from axially chiral BODIPY DYEmers: an experimental and computational study. Chem a Eur J. 2016;22(45):16089-16098. doi:10.1002/chem.201602684
Kumar J, Nakashima T, Kawai T. Circularly polarized luminescence in chiral molecules and supramolecular assemblies. J Phys Chem Lett. 2015;6(17):3445-3452. doi:10.1021/acs.jpclett.5b01452
Deng Y, Wang M, Zhuang Y, Liu S, Huang W, Zhao Q. Circularly polarized luminescence from organic micro-/nanostructures. Light: Sci Appl. 2021;10(10):76. doi:10.1038/s41377-021-00516-7
Albano G, Pescitelli G, Bari LD. Chiroptical properties in thin films of π-conjugated systems. Chem Rev. 2020;120(18):10145-10243. doi:10.1021/acs.chemrev.0c00195
Chen CF, Shen Y. Introduction to helicene chemistry. In: Helicene Chemistry. Springer; 2017:3-17.
Pescitelli G, Bari LD, Berova N. Application of electronic circular dichroism in the study of supramolecular systems. Chem Soc Rev. 2014;43(15):5211-5233. doi:10.1039/C4CS00104D
Thomas A, Chervy T, Azzini S, et al. Mueller polarimetry of chiral supramolecular assembly. J Phys Chem C. 2018;122(25):14205-14212. doi:10.1021/acs.jpcc.8b01867
Li M, Nizar S, Saha S, et al. Strong coupling of chiral Frenkel exciton for intense, bisignate circularly polarized luminescence. Angew Chem. 2022;62:6.
Condon EU. Theories of optical rotatory power. Rev Mod Phys. 1937;9(4):432-457. doi:10.1103/RevModPhys.9.432
Kirkwood JG. On the theory of optical rotatory power. J Chem Phys. 1937;5(6):479-491. doi:10.1063/1.1750060
Craig DP, Thirunamachandran T. Molecular Quantum Electrodynamics. Academic Press; 1984.
Kasha M. Energy transfer mechanism and the molecular exciton model for molecular aggregates. Radiat Res. 1964;3(4):317-331. doi:10.1111/j.1751-1097.1964.tb08155.x
Davidov AS. Theory of Molecular Excitons. Plenum Press; 1971:145.
Agranovich VM, Galanin MD. Electronic excitation energy transfer in condensed matter. Ber Bunsen Phys Chem. 1984;88(7):678-687. doi:10.1002/bbpc.19840880729
DeVoe H. Optical properties of molecular aggregates. I. Classical model of electronic absorption and refraction. J Chem Phys. 1964;07(41):393-400.
Devoe H. Optical properties of molecular aggregates. II. Classical theory of the refraction, absorption, and optical activity of solutions and crystals. J Chem Phys. 1965;11(43):3199-3208.
Fan Z, Govorov A. Plasmonic circular dichroism of chiral metal nanoparticle assemblies. Nano Lett. 2010;7(10):2580-2587. doi:10.1021/nl101231b
Kar S, Swathi K, Sissa C, Painelli A, Thomas K. Emergence of chiroptical properties in molecular assemblies of phenyleneethynylenes: the role of quasi-degenerate excitations. J Phys Chem Lett. 2018;9(16):4584-4590. doi:10.1021/acs.jpclett.8b01988
Nitzan A. Chemical Dynamics in Condensed Phases: Relaxation, Transfer and Reactions in Condensed Molecular Systems. Oxford University Press; 2006.
Schatz GC, Ratner MA. Quantum Mechanics in Chemistry. Prentice Hall; 1993.
Anzola M, Painelli A. Aggregates of polar dyes: beyond the exciton model. Phys Chem Chem Phys. 2021;23(14):8282-8291. doi:10.1039/d1cp00335f
Terenziani F, Painelli A. Supramolecular interactions in clusters of polar and polarizable molecules. Phys Rev B. 2003;68(16). doi:10.1103/physrevb.68.165405
Andrews SS. Using Rotational Averaging To Calculate the Bulk Response of Isotropic and Anisotropic Samples from Molecular Parameters. J Chem Educ. 2004;81(6):877. doi:10.1021/ed081p877
Sebastian E, Philip AM, Benny A, Hariharan M. Null Exciton Splitting in Chromophoric Greek Cross (+) Aggregate. Angew Chem Int Ed. 2018;57(48):15696-15701. doi:10.1002/anie.201810209
Greenfield JL, Wade J, Brandt JR, Shi X, Penfold TJ, Fuchter MJ. Pathways to increase the dissymmetry in the interaction of chiral light and chiral molecules. Chem Sci. 2021. doi:10.1039/d1sc02335g
Swathi K, Sissa C, Painelli A, George Thomas K. Supramolecular chirality: a caveat in assigning the handedness of chiral aggregates. Chem Commun. 2020;56(59):8281-8284. doi:10.1039/d0cc01922d
Harada N, Chen S-ML, Nakanishi K. Quantitative definition of exciton chirality and the distant effect in the exciton chirality method. J Am Chem Soc. 1975;97(19):5345-5352. doi:10.1021/ja00852a005