Thiacrown Ethers Engaged C60 through Charge Transfer: Experimental and Theoretical Study

Khaled Al Khalyfeh; Akef T Afaneh; Ali Marashdeh; Mansour H Almatarneh; Ghassab M Al-Mazaideh; Shehadeh Mizyed; Muhammad Ashram

doi:10.1021/acsomega.0c01877

Thiacrown Ethers Engaged C₆₀ through Charge Transfer: Experimental and Theoretical Study

ACS Omega. 2020 Sep 25;5(39):25049-25058. doi: 10.1021/acsomega.0c01877. eCollection 2020 Oct 6.

Authors

Khaled Al Khalyfeh¹, Akef T Afaneh², Ali Marashdeh², Mansour H Almatarneh^{3

4}, Ghassab M Al-Mazaideh^{5

6}, Shehadeh Mizyed⁷, Muhammad Ashram⁸

Affiliations

¹ Department of Chemistry, Al-Hussein Bin Talal University, Ma'an 71111, Jordan.
² Department of Chemistry, Faculty of Science, Al-Balqa Applied University, P.O. Box 19117, Al-Salt 19117, Jordan.
³ Department of Chemistry, University of Jordan, Amman 11942, Jordan.
⁴ Department of Chemistry, Memorial University, St. John's, NL A1B 3X7, Canada.
⁵ Department of Chemistry and Chemical Technology, Faculty of Science, Tafila Technical University, P.O. Box 179, Tafila 66110, Jordan.
⁶ School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Penang , Malaysia.
⁷ Department of Chemistry, Yarmouk University, Irbid 21163, Jordan.
⁸ Department of Chemistry, Mutah University, Al Karak 61710, Jordan.

Abstract

UV-Vis spectroscopy is used to study the charge transfer complexes of thiacrown ethers 1-6 with fullerene. The size of TCE1-6 and the nature of the heteroatoms (N, O and S) have been systematically changed to examine the effect of these factors on the HOMO/LUMO energy levels, the optical energy gap and the interactions between TCE's and C60. The negative and positive values of ΔS designate the structural forming method and the randomness of the free solvent molecules, respectively. Thermodynamics and stability data show that the complexes have a 1:1 ratio that has been emphasized by density functional theory calculations. Additionally, they show a synergetic interplay of donor-acceptor, π-π, and n-π interactions, which are the basis for the affinity of our novel receptors toward C₆₀. The proposed system of enzyme model suggests a development concept in the future design of enzyme model organic photovoltaic systems.