π-Conjugated Macrocycle Host–Guest Coassembly with C60 on HOPG

Abstract

Two kinds of π-conjugated macrocycles with aggregation-induced emission (AIE) properties were investigated by scanning tunneling microscopy (STM) to elucidate their self-assembly behaviors and interaction with C60 on a highly oriented pyrolytic graphite (HOPG) surface. Both TPEMC and TPEMCS could self-assemble into orderly cavity structures. However, C60 guest molecules could only successfully enter the cavity of TPEMC to form a stable TPEMC + C60 host–guest coassembly structure. Density functional theory (DFT) calculations were also used to interpret the assembly mechanisms. This work disclosed the assembly characteristic of these new types of conjugated macrocyclic compounds, which was helpful to develop new structural porous luminescent materials.

Recent advances in supramolecular fullerene chemistry

“… 212 In related work, Zeng and coworkers created ordered 2D C 60 patterns on a highly oriented pyrolytic graphite (HOPG) surface using host–guest complexes of aggregation-induced emissive macrocycles and fullerenes. 495 Rosei and coworkers employed a 2D covalent organic framework as surface-confined template to host the C 70 moieties, imposing anchoring effects on the LC growth of C 70 molecules, forming several fullerene-based LC mesophases, which cannot be observed under other conditions. 496 These findings highlight the potential of fullerene-based surface co-assemblies for developing advanced materials and functional devices.…”

Self-Assembly of Triphenylamine Macrocycles and Co-assembly with Guest Molecules at the Liquid–Solid Interface Studied by STM: Influence of Different Side Chains on Host–Guest Interaction

“…Considering that the sizes of the guest and the cavity need to be matched with each other, first, we chose C60 as the guest molecules in the host–guest assembly. In previous studies, surface complexation with C60 was successfully achieved by using macrocycles and the pore sizes were ∼1.2 nm. − In our experiments, the diameter of C60 ( d = 0.7 nm) could match both the macrocycle’s hexagonal holes ( d 2 = 1.4 nm) and the triangular cavities ( L 3 = 1.2 nm). After dropping 2 μL of a COTPA solution in HA on HOPG and then dropping 1 μL of a saturated C60 solution in HA, we did not observe any C60 molecules captured by holes or cavities at the liquid–solid interface (as shown in Figure S5).…”

Shape-responsive adsorption of an oval macrocycle co-deposited with guest molecules

“…Therefore, the fluorescence decay after adding Py is probably attributed to the intramolecular energy transfer or electron transfer after the host-guest complexation. 43,44 Conversely, it is also referred that the cavities of M1 may not trap Tp in the dilute toluene solution because the PL intensity of M1 in the mixed M1/Tp solution hardly shows any changes.…”