An Electron‐Rich Calixarene‐Based Receptor with Unprecedented Binding Affinity for Nitric Oxide
Chemistry : A European Journal
Calixarenes have found widespread application as building blocks for the design and synthesis of functional materials in host–guest chemistry. The ongoing desire to develop a detailed understanding of the nature of NO bonding to multichromophoric π‐stacked assemblies led us to develop an electron‐rich methoxy derivative of calixarene (3), which we show exists as a single conformer in solution at ambient temperature. Here, we examine the redox properties of this derivative, generate its cation radical (3+.) using robust chemical oxidants, and determine the relative efficacy of its NO binding in comparison with model calixarenes. We find that 3/3+. is a remarkable receptor for NO+/NO, with unprecedented binding efficacy. The availability of precise experimental structures of this calixarene derivative and its NO complex, obtained by X‐ray crystallography, is critically important both for developing novel functional NO biosensors, and understanding the role of stacked aromatic donors in efficient NO binding, which may have relevance to biological NO transport.
Wang, Denan; Ivanova, Lena V.; Ivanov, Maxim V.; Mirzaei, Saber; Timerghazin, Qadir K.; Reid, Scott A.; and Rathore, Rajendra, "An Electron‐Rich Calixarene‐Based Receptor with Unprecedented Binding Affinity for Nitric Oxide" (2018). Electrical and Computer Engineering Faculty Research and Publications. 521.
ADA Accessible Version
Accepted version. Chemistry : A European Journal, Vol. 24, No. 66 (November 27, 2018): 17439-17443. DOI. © 2018 Wiley. Used with permission.