Boron‐Locked Starazine – A Soluble and Fluorescent Analogue of Starphene. Issue 29 (7th April 2022)

• Record Type: Journal Article
• Authors: Feng, Yi; Zhou, Jiadong; Qiu, Honglin; Schnitzlein, Matthias; Hu, Jingtao; Liu, Linlin; Würthner, Frank; Xie, Zengqi
• Is Part Of: Chemistry. Volume 28:Issue 29(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-07
• Subjects: conjugated molecule -- electronic structure -- luminescence -- starazine -- starphene analogue; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202200770
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A starlike heterocyclic molecule containing an electron‐deficient nonaaza‐core structure and three peripheral isoquinolines locked by three tetracoordinate borons, namely isoquinoline‐nona‐starazine (QNSA), is synthesized by using readily available reactants through a rather straightforward approach. This new heteroatom‐rich QNSA possesses a quasi‐planar π‐backbone structure, and bears phenyl substituents on borons which protrude on both sides of the π‐backbones endowing it with good solubility in common organic solvents. Contrasting to its starphene analogue, QNSA shows intense fluorescence with a quantum yield (PLQY) of up to 62 % in dilute solution. Abstract : The first counterpart of starphene, namely starazine, that contains a nonaaza‐core structure and three peripheral isoquinoline units locked by three tetracoordinate borons to form a quasi‐planar backbone is described. This starazine possesses a non‐aromatic and electron‐deficient core due to the introduction of the heteroatoms replacing the corresponding carbon atoms in starphene. The transition to its lowest excited state is allowed, sharply contrasting to the starphenes, endowing fluorescent properties to this novel starlike dye molecule.