Synthesis and Self‐assembly of Benzoperylene Benzimidazoles: Tunable Morphology with Aggregation‐Induced Enhanced Emission

Abstract

Benzoperylene benzimidazoles (BPBIs) based π‐systems were synthesized and their self‐assembly in both non‐polar and polar solvents investigated. Due to the presence of donor and acceptor functional groups, BPBIs absorb light up to 600 nm and display red fluorescence (575–800 nm). Depending on the solvent and side chain, BPBIs self‐assemble into various nanostructures such as nanoribbons, nanorods, nanofibers and nanoparticles. Notably, these ordered nanostructures are formed by BPBIs in both polar and non‐polar solvents without the aid of hydrogen bonding and amphiphilic interactions due to the presence of a large rigid π‐system. Interestingly, BPBIs follow a weakly cooperative mechanism during the self‐assembly. Moreover, BPBIs show aggregation‐induced enhanced emission (AIEE) in all the self‐assembled nanostructures which is not common for rigid π‐systems.

Solvent-Mediated Chiral Self-Assembly of Nanosized π-Conjugated Polyhedral Oligomeric Silsesquioxane toward Full Spectrum Luminescence

“…Benzoperylene as a π-electron conjugation system, has well-defined luminescence properties . In this work, we synthesized benzo­[ghi]­perylene-1,2-dicarboxylic anhydride (BPA) by combining perylene and maleic anhydride in one step with nearly 100% yield .…”

Pathway Selection in Temporal Evolution of Supramolecular Polymers of Ionic π‐Systems: Amphiphilic Organic Solvent Dictates the Fate of Water

“…[22][23][24][25][26][27][28][29] On the other hand, both polar and non-polar solvent media can be used to synthesize ordered SPs for large π-systems. [30][31][32][33] Mixtures of solvents are more complex than a single solvent medium to explore the self-assembly of small molecules/ polymers. [34][35][36][37][38][39] Conversely, solvent mixtures are exciting to uncover unforeseen phenomena that cannot be observed in a single solvent.…”

“…For example, non‐polar solvent media can facilitate the formation of hydrogen‐bonded (H‐bonded) SPs, [11–21] whereas polar solvent media is used to synthesize SPs from amphiphilic molecules [22–29] . On the other hand, both polar and non‐polar solvent media can be used to synthesize ordered SPs for large π‐systems [30–33] . Mixtures of solvents are more complex than a single solvent medium to explore the self‐assembly of small molecules/polymers [34–39] .…”