TY - JOUR
T1 - Thiourea-Based Receptors for Anion Recognition and Signaling
AU - Gomez-Vega, Jancarlo
AU - Vasquez-Cornejo, Adrian
AU - Juárez-Sánchez, Octavio
AU - Corona-Martínez, David O.
AU - Ochoa-Terán, Adrián
AU - López-Gastelum, Karla A.
AU - Sotelo-Mundo, Rogerio R.
AU - Santacruz-Ortega, Hisila
AU - Gálvez-Ruiz, Juan Carlos
AU - Pérez-González, Refugio
AU - Ochoa Lara, Karen Lillian
N1 - Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.
PY - 2024/1/30
Y1 - 2024/1/30
N2 - This work reports on two thiourea-based receptors with pyridine and amine units including 1-naphthyl (MT1N) and 4-nytrophenyl (MT4N) as signaling units. For both compounds, their affinity and signaling ability toward various anions of different geometry and basicity in DMSO were studied using UV-vis, fluorescence, and 1H NMR techniques. Anion recognition studies revealed that both MT1N and MT4N have, in general, high affinities toward basic anions. In this regard, a higher acidity of the MT4N receptor was demonstrated. Furthermore, MT4N has a higher affinity for fluoride (log K1 = 5.98) than for the other anions and can effectively detect it through colorimetric changes that can be monitored by the UV-vis technique. The interaction between receptors and anions mainly involves the hydrogens of the amino and thiourea groups of the former. Complementary single-crystal X-ray diffraction studies and molecular modeling at the DFT level were also performed.
AB - This work reports on two thiourea-based receptors with pyridine and amine units including 1-naphthyl (MT1N) and 4-nytrophenyl (MT4N) as signaling units. For both compounds, their affinity and signaling ability toward various anions of different geometry and basicity in DMSO were studied using UV-vis, fluorescence, and 1H NMR techniques. Anion recognition studies revealed that both MT1N and MT4N have, in general, high affinities toward basic anions. In this regard, a higher acidity of the MT4N receptor was demonstrated. Furthermore, MT4N has a higher affinity for fluoride (log K1 = 5.98) than for the other anions and can effectively detect it through colorimetric changes that can be monitored by the UV-vis technique. The interaction between receptors and anions mainly involves the hydrogens of the amino and thiourea groups of the former. Complementary single-crystal X-ray diffraction studies and molecular modeling at the DFT level were also performed.
UR - http://www.scopus.com/inward/record.url?scp=85183038411&partnerID=8YFLogxK
U2 - 10.1021/acsomega.3c06861
DO - 10.1021/acsomega.3c06861
M3 - Artículo
C2 - 38313514
AN - SCOPUS:85183038411
SN - 2470-1343
VL - 9
SP - 4412
EP - 4422
JO - ACS Omega
JF - ACS Omega
IS - 4
ER -