Wan Yue

Hybrid rylene arrays via combination of Stille coupling and C-H transformation as high-performance electron transport materials.

Hybrid rylene arrays have been prepared via a combination of Stille coupling and C-H transformation. The ability to extend the π system along the equatorial axis of rylenes not only leads to broadened light absorption but also increases the electron affinity, which can facilitate electron injection and transport with ambient stability.

One-Pot Synthesis of Stable NIR Tetracene Diimides via Double Cross-Coupling

Tetracene tetracarboxylic diimides have been synthesized based on direct double ring extension of electron-deficient naphthalene diimides involving metallacyclopentadienes. Atomic structure and electronic transitions responsible for their NIR absorption spectra are investigated with quantum-chemical calculations. In light of their unique structure and admirable photophysical and electronic properties, this new molecular skeleton is promising candidate for n-type semiconductors.

One-Pot Facile Synthesis of Pyridyl Annelated Perylene Bisimides

Two regiospecifically pyridyl annelated perylene bisimides have been prepared in one pot by the combination of the Suzuki cross-coupling reaction and subsequent light-promoted cyclization in high yields.

Heterocyclic annelated di(perylene bisimide): constructing bowl-shaped perylene bisimides by the combination of steric congestion and ring strain.

In this paper, we present the synthesis of S- and N-heterocyclic annelated di(perylene bisimide) with extraordinary doubly bowl-shaped structures. The structures of fused PBI bowls confirmed by single-crystal X-ray structure analysis and temperature-dependent (1)H NMR are realized by the introduction of the steric congestion in nonbay regions and by the concurrent formation of the five-membered heterorings strain in bay regions. On the basis of the geometry obtained from the X-ray analysis, the maximum POAV1 pyramidalization angle is found in N-heterocyclic annelated diPBI 7, as large as 4.7 degrees , indicating the formation of two PBI bowls with significant curvatures. Furthermore, to assist the electrochemical and spectroscopic characterization of the two bowl-shaped derivatives and to assess the influence of heteroatoms on the bowl curvature, quantum-chemically optimized atomic structures, electronic properties, and optical signatures were computed with density functional theory.

Direct Functionalization of Polycyclic Aromatics via Radical Perfluoroalkylation

Direct functionalization of electron-deficient and electron-rich polycyclic aromatics via copper-mediated radical perfluoroalkylation was achieved in high yields.

Copper-Mediated Domino Process for the Synthesis of Tetraiodinated Di(perylene bisimide)

Tetraiodinated di(perylene bisimide) has been prepared from tetrabrominated perylene bisimide by the combination of Ullmann-type coupling, C-H transformation, and halogen-exchange. The crystal structure analysis confirmed that the aromatic core is quite distorted because of the electrostatic repulsion and steric encumbrance of iodine substituents in the bay regions.

One-Pot Synthesis of Well-Defined Oligo- Butadiynylene-Naphthalene Diimides

A homogeneous series of well-defined oligo-butadiynylene-NDIs containing up to five naphthalene diimides (NDIs) moieties have been efficiently synthesized in one pot by oxidative homocoupling of 1,6-di((trimethylsilyl)ethynyl)naphthalene diimides in good yields.

High performance n-type single crystalline transistors of naphthalene bis(dicarboximide) and their anisotropic transport in crystals

High-performance n-type organic single crystal transistors of a naphthalene diimide are demonstrated. The accomplished transistors exhibit electron mobility as high as 0.7 cm(2) V(-1) s(-1). The anisotropic charge transport in the elongated hexagonal crystals of the naphthalene diimide is also explored. The transport anisotropy along different directions is at least 1.6 (mobility ratio).

Direct Meta-Selective Alkylation of Perylene Bisimides via Palladium-Catalyzed C−H Functionalization

A facile palladium-catalyzed procedure for meta-selective alkylation of perylene bisimides with alkyl halides has been achieved by direct C-H functionalization.

Chiral nanoribbons based on doubly-linked oligo-perylene bisimides

A facile strategy towards conformationally stable chiral ladder-type oligo-perylene bisimides is established via copper-mediated Ullmann coupling. Absolute configurations are determined with the help of quantum-chemical calculations.