Supramolecular Nanostructures Based on Perylene Diimide Bioconjugates: From Self-Assembly to Applications

Abstract

Self-assembling π-conjugated systems constitute efficient building blocks for the construction of supramolecular structures with tailored functional properties. In this context, perylene diimide (PDI) has attracted attention owing to its chemical robustness, thermal and photo-stability, and outstanding optical and electronic properties. Recently, the conjugation of PDI derivatives to biological molecules, including oligonucleotides and peptides, has opened new avenues for the design of nanoassemblies with unique structures and functionalities. In the present review, we offer a comprehensive summary of supramolecular bio-assemblies based on PDI. After briefly presenting the physicochemical, structural, and optical properties of PDI derivatives, we discuss the synthesis, self-assembly, and applications of PDI bioconjugates.

Semiconductive and Biocompatible Nanofibrils from the Self-Assembly of Amyloid π-Conjugated Peptides

“…Numerous bioelectronic devices are composed of π-conjugated organic semiconducting nanomaterials, which allow very effective charge transfer . Among π-conjugated systems, perylene diimide (PDI)-derived molecules have received a great deal of attention for their optoelectronic, physicochemical, and/or structural properties that can be modulated by the modification of their substituents. , In addition to their chemical robustness and thermal stability, PDIs are known for their propensity to self-assemble into diverse supramolecular architectures that modulate their spectroscopic and semiconductive properties. While PDI self-assembly is mainly driven by π–π stacking interactions, it can be dramatically altered by environmental conditions, such as solvent polarity, pH, concentration, and temperature as well as the chemical nature and position of their substituents .…”

Molecular strategy towards ROMP-derived hyperbranched poly(olefin)s featuring various π-bridged perylene diimides

“…34 Moreover, in this area of research, a recent review by Bourgault and coworkers demonstrated supramolecular-nanostructural behavior and self-assembly applications of PDI-based-bioconjugate materials. 35 Functionalized and non-functionalized PDI-derivatives are rarely explored in the design and characterization of hyperbranched polymers. So far there has only been three examples of such reported polymers, which mainly focuses on the synthesis of PDI-chromophore incorporated hydrophilic branched polymer matrix or HBCPs.…”

CB[10]-driven self-assembly of a homotrimer from a symmetric organic dye: tunable multicolor fluorescence and higher solid-state stability than that of a CB[8]-included homodimer

“…[4][5][6][7][8][9][10] In the case of conjugated molecules that have a great stacking tendency in solution, accurate control of their supramolecular oligomerization through face-to-face stacking in one-dimensional (1D) space is highly valuable, because it has been well established that the stacking of conjugated systems can lead to new photoluminescence properties that are not available through single molecules, but largely related to the degree of stacking-based aggregation or polymerization. 4,[11][12][13][14][15] Currently, the self-assembly of the most simplest dimers 4,16,17 and more complicated 1D supramolecular polymers, 4,12 which are the start and end points of supramolecular polymerization, by a variety of conjugated systems has been reported. In many cases, their stacking-caused photoluminescence behaviours have been revealed to be remarkably different from those of single monomers.…”