Nitrogen-doped polycyclic aromatic hydrocarbons by a one-pot Suzuki coupling/intramolecular S_NAr reaction

Abstract

We report a new method for the synthesis of nitrogen-doped (N-doped) polycyclic aromatic hydrocarbons (PAHs) by a Suzuki coupling/intramolecular SNAr cascade reaction. A one- or two-fold [3+3] naphtho-annulation of halogenated...

Facile Synthesis of Nitrogen‐Doped Nanographenes with Joined Nonhexagons via a Ring Expansion Strategy

“…Compounds ME2 and DE2 exhibited weak absorption in the range of 400-500 nm, resulting from the extra fused fivemembered ring. The absorption peaks of ME3 and DE3 were observed at approximately 410 nm with emission peaks at 527 nm and 523 nm, respectively, resulting in a larger Stokes shift (0.68 eV for ME3, 0.65 eV for DE3) compared to the results obtained by Lindner (0.18 eV) [7] and Würthner (0.09 eV) [8] with N-doped six-membered ring, indicating a promising application in fluorescence imaging. [23] The observation of low quantum yield in DE1 and DE3 (10 % for DE1 and 7 % for DE3) was probably due to the dynamic motion of N-doped cyclooctatetraene which accelerates the nonradiative decay process from the excited state.…”

Methylene-bridged naphthotubes: new macrocyclic arenes with great potential for supramolecular chemistry

“…Supramolecular chemistry is "chemistry beyond the molecule". [1][2][3][4][5] Since the Nobel Prize in Chemistry was awarded to Pedersen, Cram, and Lehn in 1978, supramolecular chemistry has advanced significantly. As an emerging and evolving science, supramolecular chemistry has demonstrated energetic vitality and strong cross-integration capabilities and is deeply connected to chemistry, physics, biology, materials science and many other fields, forming a range of subdisciplines.…”

“…58 For example, the phenol groups of CAs are tilted and can be flipped to form diverse conformations with low barriers. There are four typical conformations of calix [4]arenes, but only the conical conformation has a cavity that can accommodate guests, and the cavities of other conformations collapse and cannot accommodate guests well. Therefore, designing and synthesizing new macrocyclic hosts with well-defined cavities is particularly important for the development and application of supramolecular chemistry.…”

ortho O-Annulated azabenzannulated perylenediimide and bisazacoronenediimide

“…1 This structure–property relationship allows material chemists to design conjugated materials with specific properties, tailored for organic electronics devices. 2 Introducing heteroatoms, 3 such as nitrogen 4 or sulfur, 5 into their core is a powerful strategy to tune their frontier orbital energy, as well as their optical, semiconducting and self-assembly properties. The inclusion of oxygen atoms 6 in the skeleton of PAHs leads to applications ranging from chiroptics 7 and spintronics 8 to organic electronics 9 and photocatalysis.…”