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Red Circularly Polarized Luminescence from Dimeric H-Aggregates of Acridine Orange by Chiral Induction

  • Sanoop Mambully Somasundaran
    Sanoop Mambully Somasundaran
    School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram 695551, India
  • Srinath V. K. Kompella
    Srinath V. K. Kompella
    Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur, Bangalore 560064, India
  • Hridya Valia Madapally
    Hridya Valia Madapally
    School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram 695551, India
  • E. Krishnan Vishnu
    E. Krishnan Vishnu
    School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram 695551, India
  • Sundaram Balasubramanian*
    Sundaram Balasubramanian
    Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Jakkur, Bangalore 560064, India
    *Email: [email protected]
  • , and 
  • K. George Thomas*
    K. George Thomas
    School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram 695551, India
    *Email: [email protected]
Cite this: J. Phys. Chem. Lett. 2024, 15, 2, 507–513
Publication Date (Web):January 8, 2024
https://doi.org/10.1021/acs.jpclett.3c03127
Copyright © 2024 American Chemical Society

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    Abstract

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    Understanding the mechanism of chirality transfer from a chiral surface to an achiral molecule is essential for designing molecular systems with tunable chiroptical properties. These aspects are explored herein using l- and d-isomers of alkyl valine amphiphiles, which self-assemble in water as nanofibers possessing a negative surface charge. An achiral chromophore, acridine orange, upon electrostatic binding on these surfaces displays mirror-imaged bisignated circular dichroism and red-emitting circularly polarized luminescence signals with a high dissymmetry factor. Experimental and computational investigations establish that the chiroptical properties emerge from surface-bound asymmetric H-type dimers of acridine orange, further supported by fluorescence lifetime imaging studies. Specifically, atomistic molecular dynamics simulations show that the experimentally observed chiral signatures have their origin in van der Waals interactions between acridine orange dimers and the amphiphile head groups as well as in the extent of solvent exposure of the chromophore.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpclett.3c03127.

    • Experimental Section; steady state spectroscopic investigations; zeta potential analysis; time-correlated single-photon counting; high-resolution transmission electron microscopy; cryo-transmission electron microscopy; atomic force microscopy; confocal microscopy; fluorescence lifetime imaging: synthesis of C16-l-valine/C16-d-valine; preparation of chiral template; microscopic images of templates; computational details; molecular dynamics simulations; simulation model; theoretical spectra calculations; theoretical absorption and CD spectra; rationalizing the preferential twist of CM-bound AO dimers; figures from computational investigations; assignment of the 465 nm band and estimation of aggregation number; additional figures from computational investigations; calculation of emission dissymmetric factor and CPL brightness; and temperature-dependent spectroscopic investigations; linear dichroism spectrum (PDF)

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