Fragmentation pattern of shape-persistent macrocycles: a mass spectrometric study

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Authors

AMATO Filippo PHULWALE Bhimrao Vaijnath MAZAL Ctibor HAVEL Josef

Year of publication 2014
Type Appeared in Conference without Proceedings
MU Faculty or unit

Faculty of Science

Citation
Description Shape-persistent macrocycles (SPMs) are organic molecules characterized by a rigid non-collapsing ring with a cavity of fixed size. The ring can be either fully or partially conjugated. The properties of such macrocycles can be altered by derivatization with suitable substituents on the ring structure [1]. SPMs have wide application as building blocks for the “bottom-up” design and development of highly organised supramolecular architectures [2], nano-materials, nano-sized molecular devices, receptors, selective catalysts, chelators, discotic liquid crystals, metal organic frameworks, etc. Systematic mass spectrometric study of the fragmentation pattern of SPMs induced by pulsed laser and/or by collisions in quadrupole ion trap (QIT) has not been carried out up to now. The aim of this work is to: i) study the laser- and collision-induced fragmentation pathways of a series of shape-persistent macrocycles, ii) search for self-assembled supramolecular aggregates and iii) study the effect of fullerene as matrix by Matrix-Assisted Laser Desorption Ionisation Quadrupole-Ion-Trap Time-of-Flight Mass Spectrometry (MALDI-QIT-TOF-MS). Collision-induced fragmentation patterns of fifteen SPMs were studied by MALDI-QIT-TOF-MS and the stoichiometry of detected fragments was determined by modelling of the isotopic pattern. It was found that the use of fullerene as MALDI matrix enhances the laser-induced fragmentation during mass spectrometric analysis. The study of the fragmentation patterns of SPMs is useful for understanding their gas-phase behaviour after laser-induced excitation.
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