journal article·2024Open access

Chirality induction to porphyrin derivatives co-confined at the air–water interface with silica nano-helices: towards enantioselective thin solid film surfaces

Michela Ottolini, Zakaria Anfar, Nitika Grover, Gabriele Magna, Manuela Stefanelli, Roberto Paolesse, Mathias O. Senge, Simona Bettini, Ludovico Valli, Reiko Oda, Gabriele Giancane

Nanoscale· Volume 16· Issue 35

Abstract

A supramolecular approach based on self-assembled structures allows the formation of large structured co-assemblies based on chiral and achiral compounds with original physicochemical features. In this contribution, an achiral and hydrophobic porphyrin was co-assembled at the air-water interface with mesoscopic silica nano-helices dispersed in the water subphase of a Langmuir trough without covalent bond formation. This procedure allowed transferring the porphyrin/nano-helix co-assemblies on a solid support within a thin hybrid layer. The interaction between the two species was characterized using spectroscopic techniques and atomic force microscopy. As evidenced by the circular dichroism measurements performed directly on solid films, tunable chirality was induced to the porphyrin aggregates according to the chirality of the silica nano-helices. When the co-assemblies were transferred on surface plasmon resonance (SPR) slides and exposed to aqueous solutions of histidine enantiomers, selective chiral discrimination was observed which was determined by the matching/mismatching between the chirality of the analyte and the helicity of the nano-helical structure.
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Research context

OpenAlex topics: Porphyrin and Phthalocyanine Chemistry · Surface Chemistry and Catalysis · Photosynthetic Processes and Mechanisms

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Biological and Environmental Sciences and Technologies (DiSTeBA), Campus Ecotekne, University of Salento, Via per Monteroni, 73100 Lecce, Italy

Univ. Bordeaux, CNRS, Bordeaux INP, CBMN, UMR 5248, F-33600 Pessac, France

School of Chemistry, Chair of Organic Chemistry, Trinity College Dublin, The University of Dublin, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Dublin, D02R590, Ireland

Department of Chemical Science and Technologies, University of Rome Tor Vergata, Via Della Ricerca Scientifica 1, 00133 Rome, Italy

Institute for Advanced Study (TUM-IAS), Focus Group – Molecular and Interfacial Engineering of Organic Nanosystem, Technical University of Munich, Lichtenbergstrasse 2a, 85748 Garching, Germany

WPI-Advanced Institute for Materials Research, Tohoku University, Katahira, Aoba-Ku, 980-8577 Sendai, Japan

Department of Cultural Heritage, University of Salento, Via D. Birago 64, 73100 Lecce, Italy

Funding

Ministero dello Sviluppo Economico · Science Foundation Ireland · Technische Universität München · Horizon 2020 Framework Programme

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