In this paper, we report the synthesis, structural characterization, and solvatochromic properties of a N-linked p-pyridiniumcalix[4]arenediol derivative 1. In the solid state, 1 forms a dimeric assembly stabilized by a network of weak H-bonding interactions involving acetonitrile solvent molecules. In solution, 1 shows a peculiar negative solvatochromism which was rationalized with the aid of TD-DFT calculations. The species responsible for this phenomenon is the monodeprotonated betainic form of 1 which is easily formed at pH close to neutrality.
Negative Solvatochromism in a N-Linked p-Pyridiniumcalix[4]arene Derivative / Iuliano, Veronica; Talotta, Carmen; Gaeta, Carmine; Soriente, Annunziata; De Rosa, Margherita; Geremia, Silvano; Hickey, Neal; Mennucci, Benedetta; Neri, Placido. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 21:8(2019), pp. 2704-2707. [10.1021/acs.orglett.9b00683]
Negative Solvatochromism in a N-Linked p-Pyridiniumcalix[4]arene Derivative
Geremia, Silvano;Hickey, Neal;
2019-01-01
Abstract
In this paper, we report the synthesis, structural characterization, and solvatochromic properties of a N-linked p-pyridiniumcalix[4]arenediol derivative 1. In the solid state, 1 forms a dimeric assembly stabilized by a network of weak H-bonding interactions involving acetonitrile solvent molecules. In solution, 1 shows a peculiar negative solvatochromism which was rationalized with the aid of TD-DFT calculations. The species responsible for this phenomenon is the monodeprotonated betainic form of 1 which is easily formed at pH close to neutrality.| File | Dimensione | Formato | |
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