1,2-硼氮杂芳烃在中国的研究进展

doi:10.6023/cjoc202212038

摘要/Abstract

稠环芳烃及其衍生物在有机光电材料领域具有广泛应用, 杂原子掺杂可有效调节稠环芳烃的物理化学性质. 用等电子体的硼氮单元取代碳碳单元, 在保持稠环芳烃芳香性的连续性的同时, 可以调节稠环芳烃的电子结构和分子间相互作用, 构建具有独特光电性质和生物活性的新型硼氮杂稠环芳烃, 既丰富了稠环芳烃的种类, 又促进了硼氮杂芳烃在光电材料、催化和生物医药等领域的应用. 近年来, 中国有机化学及材料化学领域的学者们积极参与并推动了硼氮杂芳烃的快速发展, 在硼氮杂芳烃的种类开发和应用拓展方面开展了一系列原创性的工作, 取得了瞩目的成绩. 本文综述了基于1,2-硼氮杂苯的稠环芳烃(即1,2-硼氮杂芳烃)的合成发展历史和应用研究拓展, 最后对硼氮杂芳烃领域的未来发展与应用进行了展望. 通过对硼氮芳烃在中国的发展进行系统的梳理和总结, 希望能够引起更多科研工作者对硼氮芳烃的兴趣, 期待更多的科研工作者能够加入到硼氮杂芳烃的合成拓展与应用探索中.

关键词: 硼氮杂稠环芳烃, 等电子体, 芳烃, 有机硼化学

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

引用此文

徐晓阳, 刘美艳, 李成龙, 刘旭光. 1,2-硼氮杂芳烃在中国的研究进展[J]. 有机化学, 2023, 43(5): 1611-1644.

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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图/表 66

图式1. 稠环芳烃与硼氮杂稠环芳烃

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

图1. 1,2-硼氮杂芳烃的发展脉络

Figure 1. Timeline of 1,2-BN heteroaromatics

图式2. 1,2-硼氮杂苯的Friedel-Crafts的酰基化和硝基化反应

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

图式3. 邻乙炔基苯胺为底物合成2,1-硼氮杂萘

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

图2. 六种含有单硼氮单元的硼氮杂萘的母体结构式

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

图式4. 硼乙炔基取代的2,1-硼氮杂萘的环化反应

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

图3. 嵌有2,1-硼氮杂萘的稠环芳烃

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

图4. 嵌有2,1-硼氮杂萘的星型稠环芳烃

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

图5. 硼氮键取向异构的硼氮杂芳烃

Figure 5. BN-PAHs with reversed BN orientations

图式5. 半内嵌硼氮杂萘并[2,3-d]苯并[b]噻吩37的合成

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

图式6. 双硼氮杂萘并氧杂环庚三烯类芳烃

Scheme 6. Bis-BN-naphthalene-fused oxepins

图6. 嵌有硼氮杂萘的V型稠环芳烃

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

图式7. 1,2-硼氮杂萘的合成

Scheme 7. Synthesis of 1,2-borazaronaphthalene

图式8. 9,10-硼氮杂萘的后期衍生化

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

图7. 四噻吩并硼氮杂萘

Figure 7. Tetrathieno-fused borazaronaphthalene

图8. 二芳基胺和二芳基硼基团取代的四噻吩并硼氮杂萘

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

图式9. 四苯并硼氮杂萘及其衍生物

Scheme 9. Tetrabenzo-fused borazaronaphthalene and its derivatives

图9. 文献中报道的硼氮杂蒽

Figure 9. BN-anthracenes reported in the literature

图10. 噻吩基稠合的硼氮杂蒽

Figure 10. Thieno-fused BN-anthracenes

图式10. 双硼氮掺杂蒽的合成及功能化

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

图11. 芳基稠合硼氮杂蒽

Figure 11. Aryl fused BN-anthracenes

图式11. 四苯并硼氮杂并五苯

Scheme 11. BN-doped tetrabenzopentacene

图式12. 硼氮杂并十一苯类芳烃

Scheme 12. BN-embedded eleven-ring fused heteroaromatics

图式13. 薁稠合硼氮杂蒽

Scheme 13. Azulenyl-fused BN-anthracenes

图12. 基于硼氮杂蒽的梯形共轭聚合物

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

图式14. 嵌有硼氮杂芳烃的聚合物及其在有机太阳能电池中的应用

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

图13. 文献中报道的硼氮杂菲

Figure 13. BN-phenanthrenes reported in the literature

图式15. 含有硼氮杂菲的梯形共轭聚合物

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

图式16. 基于硼氮掺杂菲的小分子和聚合物及其氟离子传感

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

图式17. 基于硼氮掺杂菲的单分子电导研究

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

图式18. 基于硼氮杂菲的阳离子型芳烃及其氧化还原研究

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

图式19. 硼氮杂菲(80e和80f)及其衍生物

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

图14. 基于硼氮杂菲的酰亚胺

Figure 14. Imide based on BN-phenanthrenes

图式20. 嵌有硼氮杂菲的薁基螺烯

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

图式21. 双硼氮掺菲的合成及其性质研究

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

图15. 硼氮杂菲的机械力致荧光变色研究

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

图16. 硼氮杂四环芳烃

Figure 16. Tetracyclic BN-PAHs

图式22. 过渡金属催化的炔环化反应构筑硼氮杂苯并[a]蒽

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

图式23. 硼氮杂苯并[a]蒽的衍生化及其指纹识别研究

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

图式24. 硼氮杂苯并[a]蒽的衍生物的机械力致变色发光和生物成像应用研究

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

图式25. 硼氮杂[4]螺烯

Scheme 25. BN-[4]helicenes

图式26. 噻吩/薁基稠合硼氮杂芳烃

Scheme 26. Thieno/azulenyl-fused BN-PAHs

图式27. 硼氮杂螺烯类芳烃

Scheme 27. BN-doped larger size helicenes

图17. 嵌有硼氮单元的低聚物

Figure 17. Oligomers with multiple BN units

图式28. 硼氮杂分子碗

Scheme 28. Bowl shaped BN-PAHs

图18. 硼氮杂苝

Figure 18. BN-doped perylenes

图式29. 基于苝酰亚胺的硼氮杂芳烃

Scheme 29. Perylene imide based BN-PAHs

图式30. 硼氮杂苝二酰亚胺

Scheme 30. BN-doped perylene diimides

图式31. 硼氮杂晕苯

Scheme 31. BN-doped coronene derivatives

图式32. 嵌有三个硼氮单元的硼氮杂晕苯

Scheme 32. BN-doped coronene bearing three BN units

图式33. 硼氮杂晕苯的水解反应

Scheme 33. Hydrolysis reaction of BN-doped coronene

图式34. 硼氮杂类晕苯芳烃

Scheme 34. BN-doped coronene-like PAHs

图式35. 硼氮杂苯并苝和硼氮杂晕苯

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

图式36. 硼氮杂苯并戊搭烯

Scheme 36. BN-doped benzopentalene

图式37. 硼氮杂呜拉嗪

Scheme 37. BN-doped ullazine

图19. 硼氮杂环戊烯稠合非那烯

Figure 19. BN-doped CP-PAHs

图式38. 硼氮杂荧蒽和硼氮杂苊烯

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

图式39. NBN型双苯并非那烯

Scheme 39. NBN-type dibenzophenylene

图式40. NBN型稠环芳烃及其在OLED中的应用

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

图式41. NBN型双螺烯

Scheme 41. NBN-fused double helicenes

图式42. 钯催化的Larock型环化反应构建NBN杂芳烃

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

图式43. NBN杂双并四苯和邻并四苯

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

图式44. NBN杂三角烯

Scheme 44. NBN-doped triangulene

图式45. 硼氮硼杂非那烯及其离子

Scheme 45. BNB-embedded phenalenyl and its anions

图式46. 硼氮硼嵌入的茚并菲

Scheme 46. BNB-embedded indenophenanthrenes

图式47. 构建含NBN型芳烃的轴手性化合物

Scheme 47. Construction of axially chiral NBN-type aromatics

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