The possibility to enhance the selectivity of phosphonate cavitands toward short-chains alcohols, namely methanol and ethanol, reducing the size of the cavity with the introduction of bulky thio-phosphonate bridging units at the upper rim is here presented. Three new mixed bridged thio-phosphonate cavitands 3POiii1PSi[H, CH3, Ph], AB-2POii2PSii[H, CH3, Ph] and AC-2POii2PSii[H, CH3, Ph] were designed, synthesized and tested as QCM sensors. The measurements show that the presence of two bulky H-bond silent Pdouble bond; length as m-dashS bridges makes the resulting AB/AC-2POii2PSii[H, CH3, Ph] cavitands effective in discriminating methanol and ethanol with respect to their longer analogs. The QCM measurements also show that the substitution of a single Pdouble bond; length as m-dashO bridge with a Pdouble bond; length as m-dashS one, as in 3POiii1PSi[H, CH3, Ph], is not sufficient, as it reduces the responses without affecting the selectivity pattern. The crystal structures of the AB-2POii2PSii[H, CH3, Ph]·MeOH and the AC-2POii2PSii[H, CH3, Ph]·MeOH complexes show that the key factors affecting the sensing performances toward alcohols of these new class of mixed-bridged phosphonate cavitands are synergistic CH–π and H-bonding interactions, as in the parent tetraphosphonate cavitands.
Supramolecular sensing of short chain alcohols with mixed-bridged thio-phosphonate cavitands / Melegari, Monica; Massera, Chiara; Pinalli, Roberta; YEBEUTCHOU MBANDA, Roger; Dalcanale, Enrico. - In: SENSORS AND ACTUATORS. B, CHEMICAL. - ISSN 0925-4005. - 179:(2013), pp. 74-80. [10.1016/j.snb.2012.10.020]
Supramolecular sensing of short chain alcohols with mixed-bridged thio-phosphonate cavitands
MELEGARI, Monica;MASSERA, Chiara;PINALLI, Roberta;YEBEUTCHOU MBANDA, Roger;DALCANALE, Enrico
2013-01-01
Abstract
The possibility to enhance the selectivity of phosphonate cavitands toward short-chains alcohols, namely methanol and ethanol, reducing the size of the cavity with the introduction of bulky thio-phosphonate bridging units at the upper rim is here presented. Three new mixed bridged thio-phosphonate cavitands 3POiii1PSi[H, CH3, Ph], AB-2POii2PSii[H, CH3, Ph] and AC-2POii2PSii[H, CH3, Ph] were designed, synthesized and tested as QCM sensors. The measurements show that the presence of two bulky H-bond silent Pdouble bond; length as m-dashS bridges makes the resulting AB/AC-2POii2PSii[H, CH3, Ph] cavitands effective in discriminating methanol and ethanol with respect to their longer analogs. The QCM measurements also show that the substitution of a single Pdouble bond; length as m-dashO bridge with a Pdouble bond; length as m-dashS one, as in 3POiii1PSi[H, CH3, Ph], is not sufficient, as it reduces the responses without affecting the selectivity pattern. The crystal structures of the AB-2POii2PSii[H, CH3, Ph]·MeOH and the AC-2POii2PSii[H, CH3, Ph]·MeOH complexes show that the key factors affecting the sensing performances toward alcohols of these new class of mixed-bridged phosphonate cavitands are synergistic CH–π and H-bonding interactions, as in the parent tetraphosphonate cavitands.File | Dimensione | Formato | |
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