Recent Advance of 1,2-BN Heteroaromatics in China

doi:10.6023/cjoc202212038

Abstract

Polycyclic aromatic hydrocarbons (PAHs) and their derivatives are widely used in the field of organic optoelectronic materials, and the photophyscial properties of polycyclic aromatic hydrocarbons can be effectively modified by heteroatomic doping. By replacing carbon carbon (CC) units with an isoelectronic and isostructural boron nitrogen (BN) units, the electronic structure and intermolecular interactions of PAHs can be fine-tuned, resulting in new BN-heteroaromatics with unique optoelectronic properties and bioactivity. BN/CC isosterism can not only enrich the famlily of heteroaromatics but also promote their applications in the fields of optoelectronic, catalysis and biomedical applications. In particular, the researchers from China have engaged and promoted the development of boron/nitrogen-doped heteroaromaics, leading to some great results. The recent advance of 1,2-BN heteroaromatics in China from the chemistry perspective is summarized, including the synthetic development of 1,2-BN heteroaromatics, as well as their applications in variety of research fields. In the end, the development prospects of BN-heteroaromatics are pointed out. Through highlighting these advances of boron/nitrogen-doped heteroaromaics in China, it is hoped that more researchers will be interested in the synthesis and application of boron/nitrogen-doped heteroaromaics. It is also hoped that this review would stimulate the conversation and cooperation between the chemists and material scientists in the related fields.

Key words: boron/nitrogen doped polycyclic aromatic hydrocarbon, isosterism, aromatics, organoboron chemistry

Cite this article

Xiaoyang Xu, Meiyan Liu, Chenglong Li, Xuguang Liu. Recent Advance of 1,2-BN Heteroaromatics in China[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1611-1644.

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Fig. & Tab. 66

Scheme 1. Polycyclic aromatic hydrocarbons and boron/nitrogen doped polycyclic aromatic hydrocarbons

Figure 1. Timeline of 1,2-BN heteroaromatics

Scheme 2. Friedel-Crafts acylation and nitration of 1,2-aza- borine

Scheme 3. Synthesis of 2,1-borazaronaphthalene using o-ethynylaniline as substrate

Figure 2. Six parental BN isosteres of naphthalene bearing one BN unit

Scheme 4. Cycloadditions of B-ethynyl-2,1-borazaronaphthalene

Figure 3. Polycyclic aromatic hydrocarbons embedded with 2,1-borazaronaphthalene

Figure 4. Star-shaped polycyclic aromatic hydrocarbons embedded with 2,1-borazaronaphthalene

Figure 5. BN-PAHs with reversed BN orientations

Scheme 5. Synthesis of semi-embedded borazaronaphthalene [2,3-d]benzo[b]thiophene 37

Scheme 6. Bis-BN-naphthalene-fused oxepins

Figure 6. V-type PAHs embedded with BN-naphthalene

Scheme 7. Synthesis of 1,2-borazaronaphthalene

Scheme 8. Late stage derivatization of 9,10-borazaronaphthalene

Figure 7. Tetrathieno-fused borazaronaphthalene

Figure 8. Tetrathieno-fused borazaronaphthalene bearing a diarylamine and/or diarylboron groups

Scheme 9. Tetrabenzo-fused borazaronaphthalene and its derivatives

Figure 9. BN-anthracenes reported in the literature

Figure 10. Thieno-fused BN-anthracenes

Scheme 10. Synthesis and functionalization of bis-BN-anthracenes

Figure 11. Aryl fused BN-anthracenes

Scheme 11. BN-doped tetrabenzopentacene

Scheme 12. BN-embedded eleven-ring fused heteroaromatics

Scheme 13. Azulenyl-fused BN-anthracenes

Figure 12. Ladder-type conjugated polymers based on BN-anthracenes

Scheme 14. Polymer embedding BN-aromatics and their application in organic solar cells

Figure 13. BN-phenanthrenes reported in the literature

Scheme 15. Ladder-type conjugated polymers based on BN-phenanthrenes

Scheme 16. Small molecules and polymers based on BN-phenanthrenes and their fluorine ion sensor

Scheme 17. Studies of single molecule conductivity properties of BN-phenanthrene

Scheme 18. Cationic PAHs based on BN-phenanthrenes and their redox properties

Scheme 19. BN-phenanthrenes (80e and 80f) and their derivatives

Figure 14. Imide based on BN-phenanthrenes

Scheme 20. Azulene-based helicenes embedding with BN-phenanthrene

Scheme 21. Synthesis of bis-BN-phenanthrenes and their properties

Figure 15. PAHs embedded BN-phenanthrenes featuring me- chanochromic luminescence

Figure 16. Tetracyclic BN-PAHs

Scheme 22. Construction of BN-doped tetraphene by transition metal catalyzed alkyne cyclization

Scheme 23. Derivatization of BN-tetraphene and fingerprint imaging studies

Scheme 24. Mechanochromic luminescence and bioimaging applications of BN-tetraphene derivatives

Scheme 25. BN-[4]helicenes

Scheme 26. Thieno/azulenyl-fused BN-PAHs

Scheme 27. BN-doped larger size helicenes

Figure 17. Oligomers with multiple BN units

Scheme 28. Bowl shaped BN-PAHs

Figure 18. BN-doped perylenes

Scheme 29. Perylene imide based BN-PAHs

Scheme 30. BN-doped perylene diimides

Scheme 31. BN-doped coronene derivatives

Scheme 32. BN-doped coronene bearing three BN units

Scheme 33. Hydrolysis reaction of BN-doped coronene

Scheme 34. BN-doped coronene-like PAHs

Scheme 35. BN-doped perylene and BN-doped coronene

Scheme 36. BN-doped benzopentalene

Scheme 37. BN-doped ullazine

Figure 19. BN-doped CP-PAHs

Scheme 38. BN-doped fluoranthene and BN-doped acenaphthene

Scheme 39. NBN-type dibenzophenylene

Scheme 40. NBN-type PAHs and their applications in OLED

Scheme 41. NBN-fused double helicenes

Scheme 42. Construction of NBN-type heteroaromatics by palladium catalyzed Larock-type cyclization

Scheme 43. NBN-doped bis-tetracene and peri-tetracene

Scheme 44. NBN-doped triangulene

Scheme 45. BNB-embedded phenalenyl and its anions

Scheme 46. BNB-embedded indenophenanthrenes

Scheme 47. Construction of axially chiral NBN-type aromatics

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1,2-硼氮杂芳烃在中国的研究进展