Self-Assembly of Crystalline Vesicles from Nonplanar π-Conjugated Nanocycles

Abstract

There is a great demand for self-assembled carbon nanomaterials because of their importance in optoelectronics, biomaterials, and so forth. Herein, we report a novel type of self-assembled, nanoscale, crystalline vesicle from nonplanar π-conjugated nanocycles. We designed four different structural [8]cycloparaphenylenes ([8]CPPs) molecules and demonstrated that these nonplanar π-conjugated CPP nanocycles could self-assemble into multilamellar, crystalline vesicles in tetrahydrofuran (THF)/H 2 O mixed solvent. The critical driving force for the assembly of nanoscale CPP vesicles is crystallization and π-π interaction of nonplanar, nanocyclic molecules. The size of CPP vesicles could be regulated by changing water content, temperature, and concentration in solution. Our data demonstrate that these π-conjugated nanocycle-based vesicles show a remarkable ability to enter cells in an energy-or temperature-independent manner and kill cancer cells. When the side groups of the CPP molecule were changed, the CPP vesicles showed a large difference in the cytotoxicity, and two CPP vesicles could effectively kill cancer cells as well as first-class antitumor agents.

Highly Efficient Blue Organic Light-Emitting Diode Based on a Pyrene[4,5- d ]Imidazole-Pyrene Molecule

“…1,2 The rigid planar structure and flat π-system of the pyrene-based component results in favorable π-electron flow, flexible self-assembly, and excellent photoelectric properties, such as bright emission, efficient excimer formation, and special-stacking topological configuration. [3][4][5][6][7] Pyrene-based materials have been widely applied as biological probes and fluorescent sensors because of their tunable fluorescence in response to environmental alteration. [8][9][10] Pyrene [4,5-d]imidazolebased organic dyes are also suitable in the applications of dye-sensitized solar cells owing to their rigid structure.…”

Self‐Assembly of Peapod‐like Micrometer Tubes from a Planet‐Satellite‐type Supramolecular Megamer

“…Supramolecular polymers (SPs), which are based on monomeric or macromonomeric units held together with directional and reversible secondary interactions, can respond to external stimuli in a way that cannot be achieved by traditional macromolecules [1–25] . Accordingly, SPs have some unique and dynamic characteristics such as self‐healing ability, ease of degradation, and reversibility, which have potential applications in recyclable/renewable materials, drug delivery, light‐harvesting, and catalysis [2, 3, 15–25] .…”

Side-chain meta[6]cycloparaphenylene-based nanoring-containing polymers

“…[1][2][3][4] The redox, optical, self-assembly, and charge-transport properties of these curved aromatic molecules can be significantly modulated compared with their non-planar counterparts, as evidenced by various curved carbon allotropes, such as carbon nanotubes, 5 nanobelts, [6][7][8][9] nanobowls, [10][11][12][13] and nanorings. [14][15][16] Among these allotropes, cycloparaphenylenes (CPPs), often referred to as carbon nanorings/nanohoops, have been initially envisioned as the simplest building blocks for the size-selective growth of armchair carbon nanotubes. [17][18][19][20][21] CPPs are some of the most representative molecular forms largely owing to their special topology and size-dependent physicochemical properties.…”