Fluorescent nano-sized aggregates of halogen bonded complexes formed using perfluoropropyl iodides: a systematic comparison between two isomeric halogen bond acceptors, aniline and 4-methyl pyridine

Fan H. Nurtay L. Daniyeva N. Benassi E.
26 May 2023 Royal Society of Chemistry

Physical Chemistry Chemical Physics
2023 #25 Issue 25 16938 - 16951 pp.

The halogen bonds (XB) formed by the two isomers 4-methyl pyridine (MePy) and aniline (ANL) with heptafluoro-1-propyl iodide (n-C₃F₇I) and heptafluoro-2-propyl iodide (iso-C₃F₇I) were investigated using vibrational (FT-IR and Raman) spectroscopy and quantum mechanical calculations. While these two isomers indicated a distinctive impact on the ring related vibrations, molecular electrostatic potential, frontier molecular orbitals, intermolecular electron density delocalisation and consequential charge transfer upon halogen bonding with n-C₃F₇I and iso-C₃F₇I, the dramatic intermolecular charge transfer (CT) occurring on the MePy involved XB systems demonstrated an ion-pair like aggregation. Such aggregation, after 72 h and longer after mixing, leads to an emission of fluorescence for both [MePy·C₃F₇I] systems. The resulting nano-sized aggregates were characterised using UV-Vis absorption and fluorescence spectroscopy along with scanning and transmittance electron microscopy (SEM and TEM), wherein, the XB complex with iso-C₃F₇I showed a faster and more severe aggregation due to a stronger CT than that with n-C₃F₇I. The present work is the first case of aggregation induced emission (AIE) due to aggregation of XB complexes formed by small neutral molecules.

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Chemistry Department, School of Sciences and Humanities, Nazarbayev University, Astana, 010000, Kazakhstan
Core Facility, Nazarbayev University, Astana, 010000, Kazakhstan
Faculty of Natural Sciences, Novosibirsk State University, Novosibirsk, 630090, Russian Federation

Chemistry Department
Core Facility
Faculty of Natural Sciences

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