Self-assembled multicolor nanoparticles based on functionalized twistacene dendrimer for cell fluorescent imaging

Abstract

A series of twistacene-functionalized dendrimers were successfully synthesized and characterized. The model molecule DBPy has a twisted configuration with a torsional angle of 27.69°between pyrene and naphthalene units. The resulting compounds TPPh, TTPy, OTPy and TOPhP can self-assemble into organic nanoparticles through re-precipitation method and emit strong blue, cyan, green and red fluorescence in water, respectively. Additionally, the obtained multicolor nanoparticles showed low cytotoxicity and good photostability that selectively flow into the membrane and cytoplasm of HeLa cells, indicating the feasibility and efficiency in fluorescence imaging. This study might be a new avenue for the design of three-dimensional branched conjugated molecule and specific location imaging in living cell.

Electron‐Rich Twistacene‐Modified Arylboron Donor–Acceptor Systems: Synthesis, Photophysics, and Electroluminescence with Hot Exciton Response

“…Subsequently, Xiao et al. also synthesized a library of twistacene‐modified dendrimers, which self‐assembled into multi‐color nanoparticles for imaging specific location in living cells . Surveying the smallest twistacene in this family, 11‐methyl‐9,14‐diphenyldibenzo[ de , qr ]tetracene ( 1 , Scheme ), we find that the electron density mainly concentrates on the benzo[ f ]tetraphene moiety, based on DFT calculations (Figure ), indicating that the electrons of the lateral phenyl units and cycle V flow to the benzo[ f ]tetraphene moiety.…”

Pyridazine‐Containing Diazatwistanthracene and Tetraazatwisttetracene: Synthesis, Crystal Structures and Third Order Non‐linear Optical Properties

“…Obviously, the crystal structure of compound TPPA (CCDC: 1873379) belongs to a monoclinic space group P2(1)/c with unit cell parameters of a =9.4908(8) Å, b =25.2835(18) Å, c =10.2165(7) Å, α = γ =90°, β =99.542(3)°. Note that the obtained molecule TPPA exhibited twisted configuration, which is similar with the reported twistacenes …”

Dimesitylboryl‐Decorated Azaarene: Synthesis, Enhanced Stability and Optoelectronic Property

“…As for the precursors, they feature the maximum absorption and emission peaks at 515 nm/570 nm for 3 and 448 nm/475 nm for 6 , respectively (Figure S1). Compared with molecule 2,7‐di‐ tert ‐butyl‐11‐methyl‐9,14‐diphenyldibenzo[ de , qr ] tetracene, all the intermediates 3 / 6 and desired compounds 5 / 7 exhibit obvious bathochromic‐shift absorption and emission, which could be assigned to the introduction of heteroatoms and the enhancement of the π‐conjugation. In addition, molecules 5 and 3 also display red‐shift absorption and emission compared with their corresponding analogues 7 and 6 .…”