Supramolecular Assemblies for Electronic Materials

Abstract

This work presents a synergy between organic electronics and supramolecular chemistry, in which a host–guest complex is designed to function as an efficacious electronic material. Specifically, the noncovalent recognition of a fullerene, phenyl‐C61‐butyric acid methyl ester (PC61BM), by an alternating perylene diimide (P)‐bithiophene (B) conjugated macrocycle (PBPB) results in a greater than five‐fold enhancement in electron mobility, relative to the macrocycle alone. Characterization and quantification of the binding of fullerenes by host PBPB is provided alongside evidence for intermolecular electronic communication within the host–guest complexes.

The Pink Box: Exclusive Homochiral Aromatic Stacking in a Bis-perylene Diimide Macrocycle

“… 22 Coupled with their renowned electron-accepting and photophysical properties, PDIs are ubiquitous organic building blocks for next-generation semiconductor and optoelectronic materials. 23 − 26 …”

“…In the latter class, perylene diimides (PDIs) are important targets because they are robust, economic organic dyes with a readily functionalizable scaffold . Coupled with their renowned electron-accepting and photophysical properties, PDIs are ubiquitous organic building blocks for next-generation semiconductor and optoelectronic materials. − …”

Selective photoinduced charge separation in perylenediimide-pillar[5]arene rotaxanes

“…One approach to developing our understanding in this avenue of research is to create assemblies composed of molecular components that exhibit redox activity and/or optical properties that can be studied by a combination of spectroscopic and electrochemical techniques. In this regard, supramolecular assemblies based on redox-active molecules have been developed, notably for their potential in photosynthetic light harvesting 2,[8][9][10][11] and in organic electronics [12][13][14] . In turn, molecular dyads that comprise both electron-accepting and electron-donating groups are attractive for these purposes, potentially allowing for energy conversion following a photochemical reaction 5,15,16 .…”

Supramolecular Purification and Regioselective Functionalization of Fullerenes and Endohedral Metallofullerenes

“…Recently, a supramolecular assembly of PCBM-C 60 with a polyaromatic macrocycle has shown good electron mobility and film morphologies suitable for future electronic applications. 136 Photonic Liquid Crystals Fullerene-based liquid crystals with highly ordered columnar assemblies of the fullerene units are interesting materials for organic electronics and, especially, photovoltaic applications if oriented at surfaces. 137 In most of the work reported so far, only C 60 has been used and the strong influence of the degree of substitution of C 60 on the liquid-crystalline properties has been demonstrated.…”