The design of synthetic, monovalent host-guest molecular recognition pairs is still challenging and of particular interest to inquire into the limits of the affinity that can be achieved with designed systems. In this regard, cucurbit[7]uril (CB[7]), an important member of the host family cucurbit[n]uril (CB[n], n = 5-8, 10, 14), has attracted much attention because of its ability to form ultra-stable complexes with multiple guests. The strong hydrophobic effect between the host cavity and guests, ion-dipole and dipole-dipole interactions of guests with CB portals helps in cooperative and multiple noncovalent interactions that are essential for realizing such strong complexations. These highly selective, strong yet dynamic interactions can be exploited in many applications including affinity chromatography, biomolecule immobilization, protein isolation, biological catalysis, and sensor technologies. In this review, we summarize the progress in the development of high affinity guests for CB[7], factors affecting the stability of complexes, theoretical insights, and the utility of these high affinity pairs in different challenging applications.

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Biosensors based on a field‐effect transistor platform allow continuous monitoring of biologically active species with high sensitivity due to the amplification capability of detected signals. To date, a large number of sensors for biogenic substances have used high‐cost enzyme immobilization methods. Here, highly sensitive organic field‐effect transistor (OFET)‐based sensors functionalized with synthetic receptors are reported that can selectively detect acetylcholine (ACh+), a critical ion related to the delivery of neural stimulation. A cucurbit[6]uril (CB[6]) derivative, perallyloxyCB[6] ((allyloxy)12CB[6], AOCB[6]), which is soluble in methanol but insoluble in water, has been solution‐deposited as a selective sensing layer onto a water‐stable p‐channel semiconductor, 5,5′‐bis‐(7‐dodecyl‐9H‐fluoren‐2‐yl)‐2,2′‐bithiophene layer. The OFET‐based sensors exhibit a detection limit down to 1 × 10–12 m of ACh+, which is six orders of magnitude lower than that of ion‐selective electrode‐based sensors. Moreover, these OFET‐based sensors show highly selective discrimination of ACh+ over choline (Ch+). The findings demonstrate a viable method for the fabrication of OFET‐based biosensors with high sensitivity and selectivity, and allow for practical applications of OFETs as high‐performance sensors for biogenic substances.

Hydrogen-bonded interactions in para-substituted calix[n]arenes (CX[n]) (n = 4, 5) and their thia analogues are analyzed using the recently proposed molecular tailoring approach. The cooperative contribution toward the hydrogen-bonding network within the CX[5] host is shown to be nearly 5 times larger than that in its thia analogue. Hydrogen bond strengths in the O-H···O network are enhanced on substitution of an electron-donating group. The cooperativity contributions are reflected in the electron density at the bond critical point in the quantum theory of atoms in molecules.