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Promoting effects of the hydroxymethyl group on the fluorescent signaling recognition of anions by thioureas

โœ Scribed by Xuhong Qian; Fengyu Liu

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
259 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A series of novel fluorescent naphthylthioureas 1-4 with hydroxymethyl groups was designed and synthesized. Upon complexation with anions, 1-4 showed strong fluorescence enhancements in the order: 1>2>3:4, which is consistent with the number of hydroxymethyl groups contained in their structures. Hydroxymethyl groups have an important influence on the compounds' trans-trans or trans-cis conformations, and their action to promote the fluorescence signaling recognition of the thioureas for anions might be caused by their preorganizing the intramolecular protons of the receptor in favor of sites of the trans-trans conformation ready for hydrogen bond formation with the anions. Thioureas 1 to 4 had favorable selectivities for certain anions, which relied on the net charge and Brfnsted basicity of the anions.

๐Ÿ“œ SIMILAR VOLUMES

Solvent effect on the conformation of th
Solvent effect on the conformation of the hydroxymethyl group established by molecular dynamics simulations of methyl-ฮฒ-D-glucoside in water
โœ L. M. J. Kroon-Batenburg; J. Kroon ๐Ÿ“‚ Article ๐Ÿ“… 1990 ๐Ÿ› Wiley (John Wiley & Sons) ๐ŸŒ English โš– 470 KB ๐Ÿ‘ 2 views

Molecular dynamics simulations of methyl-P-D-glucoside in water are performed. Although the tg conformation of the hydroxymethylgroup is found to be the lowest in energy for the isolated molecule, it appears to be unstable in water. The well-known absence of a significant amount of the tg conformati