Recent Advance in the Synthesis of Ullazine and Its Derivatives

doi:10.6023/cjoc202306020

Abstract

Polycyclic aromatic hydrocarbons (PAHs) have been widely used in the field of organic electronics, due to their unique electronic and optical properties. Doping heteroatom is a popular way to modify the electronic structures and the properties of the PAHs. The resulting heteroaromatics exihit tunable physicochemical, optical, and electrochemical properties. Among the heteroatoms embedded in the scaffold of PAHs, nitrogen atom is the most common one. Ullazine, also known as indolizino[6,5,4,3-ija]quinoline, is isoelectronic with pyrene. In recent years, ullazine and its derivatives have drawn a lot attention due to its outstanding performance in dye-sensitized solar cells. The synthesis methods of ullazine developed in recent years are presented, and the overview of the current available synthetic methods of ullazine is summarized in detail.

Key words: ullazine, heteroaromatics, polycyclic aromatic hydrocarbons

Cite this article

Zimeng Shao, Yuanhui Wang, Haiying Wang, Peipei Cui, Xuguang Liu. Recent Advance in the Synthesis of Ullazine and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3679-3694.

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Fig. & Tab. 24

Figure 1. Indolizino[3-ija]quinoline (ullazine)

Scheme 1. Synthesis of ullazine by Balli and Zeller et al. using Friedel-Crafts alkylation and the mechanisms of key steps

Scheme 2. Synthesis of dibenzo[d,k]ullazines by Hongjun Ren?s group using Friedel-Crafts arylation and the mechanisms of key step

Scheme 3. Synthesis of ullazine by chromium-mediated alkyne benzannulation developed by Tamotsu Takahashi?s group

Scheme 4. Synthesis of ullazine by indium(III) chloride-mediated alkyne benzannulation developed by Gr?tzel?s group

Scheme 5. Improved synthesis of ullazine by Nazeeruddin?s group

Scheme 6. Functionalization ullazine through Vilsmeier-Haack reaction reported by Delcamp?s group

Scheme 7. Synthesis of ullazine through C—H bond functionalization reaction reported by Jinsong You?s group

Scheme 8. Mechanism of synthesis of ullazine through C—H bond functionalization reaction

Scheme 9. Synthesis of ullazine through visible light mediated twofold annulation reaction reported by K?nig?s group

Scheme 10. Mechanism of visible light mediated annulation to ullazine reported by K?nig?s group

Scheme 11. Synthesis of ullazine through aryne benzannulation reported by Ge Gao?s group

Scheme 12. Mechanism of synthesis of ullazine through alkyne benzannulation

Scheme 13. Synthesis of ullazine through [3+2] cycloaddition reaction reported by Müllen and Feng et al.

Scheme 14. Synthesis of ullazine-embedded corannulene through [3+2] cycloaddition reaction reported by Ito and Nozaki et al.

Scheme 15. Synthesis of ullazine reported by Jiaobing Wang?s group

Scheme 16. Synthesis of ullazine-based helicene reported by Jiaobing Wang?s group

Scheme 17. Synthesis of ullazine and related D-A polymers through photochemical cyclodehydrochlorination reaction reported by Morin?s group

Scheme 18. Synthesis of ullazine-embedded linear and helical graphene nanoribbons through photochemical cyclodehydrochlorination reaction reported by Morin?s group

Scheme 19. Synthesis of ullazine derivatives through metal catalyzed direct arylation reaction reported by St?pień?s group

Scheme 20. Synthesis of ullazine derivatives through 1,3-diplor cycloaddition reaction reported by Marcin St?pień?s group

Scheme 21. Synthesis of tetra-substituted ullazine derivatives through Rh-catalyzed two-step sequences reported by Wang Zhou?s group

Figure 2. Heteroatom-doped ullazine derivatives

Figure 3. Boron-doped ullazine derivatives

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