TIPS-Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes

被引：4

作者：

Ahrens, Lukas ^{[1
]}

Maier, Steffen ^{[1
]}

Misselwitz, Erik ^{[1
]}

Oeser, Thomas ^{[1
]}

Rominger, Frank ^{[1
]}

Freudenberg, Jan ^{[1
]}

Bunz, Uwe H. F. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] Heidelberg Univ, Ctr Adv Mat CAM, Neuenheimer Feld 225, D-69120 Heidelberg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 41期

关键词：

aromaticity; azaacenes; electronic coupling; peri-bisacenes; semiconductors; SINGLET-EXCITON-FISSION; ORBITAL ENERGY-LEVELS; CRYSTAL PACKING; ACENES; BISTETRACENE; TRANSISTORS; PENTACENE; OXIDATION;

D O I：

10.1002/chem.202101246

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki-coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel-Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS-ethynyl)-substituted naphtha[1,8-gh:5,4-g ' h ']diquinoline and naphtho[1,8-bc:5,4-b ' c ']diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs.

引用

页码：10569 / 10573

页数：5

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