杂原子掺杂共轭碳纳米环的合成与性质研究进展

doi:10.6023/cjoc202205006

摘要/Abstract

设计与合成具有特定结构的大环化合物既是超分子化学研究的一个重点, 也是合成化学与材料化学领域的重要机遇和挑战. 作为碳纳米管的最小片段, 径向共轭碳纳米环及环带结构引起化学家广泛的研究兴趣, 催生系列自下而上的精确合成策略, 但这些纳米环及环带大多仅由苯和简单多环芳烃基元组成, 其光电性质调控主要依赖环尺寸的变化, 限制了后续的功能开发及应用. 在此基础上, 近年来, 结构与性质更加多元的杂原子掺杂碳纳米环逐渐成为新的研究热点. 围绕含杂原子共轭碳纳米环的设计、合成与性质研究展开, 重点介绍了引入芳杂环单元如吡啶、噻吩、呋喃、咔唑、苯并噻二唑、屈并二噻吩、1,2-硼氮芳杂环、二酮吡咯并吡咯、卟啉、苝二酰亚胺、萘并二噻吩二酰亚胺等对纳米环性质的影响, 特别是: (1)杂原子引入对纳米环光谱和氧化还原电势的影响; (2)纳米环拓扑结构的变化引起组装行为的改变, 进而带来新性质. 杂原子掺杂共轭纳米环的设计与合成既可为有机光电材料研究提供理想骨架, 同时也为多功能超分子体系的可控构建提供新基元.

关键词: 碳纳米环, 径向共轭, 芳杂环, 杂原子掺杂

As structural models for carbon nanotube segments, radially conjugated carbon nanohoops have received much attention from chemists, which led to a series of bottom-up synthetic strategies. However, most of these nanohoops are composed only of benzene and simple polyaromatic hydrocarbon moieties. Modulation of the optoelectronic properties is mainly dependent on the variation of ring size, which greatly limits the functional development and application of conjugated nanohoops. In recent years, syntheses and property study of heteroatom-doped carbon nanohoops have become a new research hotspot. The design, synthesis and properties of conjugated nanohoops involving heterocyclic subunits such as pyridine, thiophene, furan, carbazole, benzothiadiazole, chrysenylene, 1,2-azaborine heterocycle, diketopyrrolopyrrole, porphyrin, perylene diimide, and naphthodithiophene diimide, etc. are reviewed. Most of these nanohoops have special topological structures. The introduction of heteroatoms not only significantly improves their optoelectronic properties, but also regulates their assembly, leading to new skeletons for multifunctional supramolecular systems and organic materials.

Key words: carbon nanohoops, radial conjugation, aromatic heterocycle, heteroatom-doping

引用此文

张慧君, 林建斌. 杂原子掺杂共轭碳纳米环的合成与性质研究进展[J]. 有机化学, 2022, 42(11): 3437-3455.

Huijun Zhang, Jianbin Lin. Syntheses and Properties of Heteroatom-Doped Conjugated Nanohoops[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3437-3455.

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图/表 21

图1. 大环分子的研究历程

Figure 1. History of research on macrocyclic compounds

图2. 基于芳香杂环的柱状纳米环结构设计

Figure 2. Design of columnar nanocyclic structures based on aromatic heterocyclic units

图3. 低张力大环芳构化策略

Figure 3. Bent precursor-aromatization strategies

图4. 金属有机大环化策略

Figure 4. Organometallic macrocyclization strategies

图5. 含吡啶或2,2'-联吡啶基元共轭纳米环的合成[26,28-29,32]

Figure 5. Synthesis of conjugated nanohoops containing pyridine or 2,2'-bipyridine moieties

Entry	Compound	λ_max^a/nm	ε/(L•mol^－1•cm^－1)	λ_em/nm	E_HOMO^b/eV	E_LUMO^b/eV
1	13a (aza[8]CPP)	345	2.8×10⁴	541	－5.25	－2.03
2	13b (1,15-diaza[8]CPP)	349	9.2×10⁴	544	－5.27	－2.08
3	13c (1,15,31-triaza[8]-CPP)	353	1.1×10⁴	542	－5.31	－2.15
4	[13a-Me]OTf	345	2.9×10⁴	598	－5.36	－2.92
5	[13b-Me₂]OTf₂	350	4.9×10⁴	630	－5.63	－3.07
6	13d (aza[6]CPP)	342	5.5×10⁴	—	－4.98	－2.14
7	[13d-Me]OTf	343	2.3×10⁴	—	－5.39	－2.86

表1. 含吡啶基元共轭纳米环13a~13d氮甲基化前后光电性质对比

Table 1. Comparison of the photoelectric properties of 13a~13d before and after N-methylation

图6. 含邻二氮菲基元共轭纳米环的合成[33]

Figure 6. Synthesis of o-phenanthroline-containing nanohoops

图7. 含五元杂环纳米环的合成[35???-39]

Figure 7. Synthesis of nanohoops containing five-membered heterocycles

Entry	Compound	λ_max/nm	ε/(L•mol^－1•cm^－1)	λ_em/nm	Φ_F/%	E_HOMO^a/eV	E_LUMO^a/eV
1	25a ([4]CPT)	333 (C₆H₁₂)	—	546	—	－5.01	－1.74
2	25b ([5]CPT)	350 (C₆H₁₂)	—	510	—	－5.00	－1.82
3	25c ([6]CPT)	362 (C₆H₁₂)	—	488	—	－4.97	－1.90
4	27a ([3]CP₂T)	346 (THF)	2.4×10⁴	523	27	－5.04	－1.76
5	27b ([4]CP₂T)	354 (THF)	3.7×10⁴	472	37	－5.13	－1.71
6	28a ([3]CP₂S)	365 (THF)	2.1×10⁴	560	8	－5.01	－1.82
7	28b ([4]CP₂S)	370 (THF)	2.8×10⁴	492	13	－5.13	－1.78
8	29 ([3]CP₂E)	371 (THF)	2.7×10⁴	555	34	－4.61	－1.65

表2. 含噻吩或硒吩基元共轭纳米环[n]CPT、[n]CP2T、[n]CP2S和[n]CP2E的光电性质对比

Table 2. Comparison of the optoelectronic properties of conjugated nanorings [n]CPT, [n]CP2T, [n]CP2S and [n]CP2E containing thiophene or selenophene units

图8. 含咔唑或二苯并噻吩纳米环的合成[41-42,45](其中光谱数据均在CHCl3中测得)

Figure 8. Synthesis of carbazole- and dibenzothiophene-containing nanohoops (the spectral data were measured in CHCl3)

图9. 含咔唑封端或八字形纳米环的合成[46-47](其中光谱数据均在CH2Cl2中测得)

Figure 9. Synthesis of carbazole-containing capped and lemniscular-shaped nanohoops (the spectral data were measured in CH2Cl2)

图10. 含苯并噻二唑单元共轭纳米环及双层纳米环的合成[48??-51](光谱数据在CH2Cl2或CHCl3中测得)

Figure 10. Synthesis of benzothiadiazole-containing nanohoops and bilayer nanohoops (the spectral data were measured in CH2Cl2 or CHCl3)

图11. 含1,8-二氮杂芘或屈并二噻吩单元的共轭纳米环的合成[52-53]

Figure 11. Synthesis of 1,8-diazopyrene- and chrysenedithiophene-containing nanohoops

图12. 含1,2-氮杂硼烷杂环的纳米环[55](其中光谱数据在CH2Cl2中测得)

Figure 12. Synthesis of 1,2-azaborine heterocycle-containing nanohoops (the spectral data were measured in CH2Cl2)

图13. 给体-受体共轭纳米环C-DPP的合成[56]

Figure 13. Synthesis of diketopyrrolopyrrole-based donor-acceptor nanohoops C-DPP

图14. 含卟啉单元共轭纳米环的合成[59?-61]

Figure 14. Synthesis of porphyrin-based conjugated nanohoops

Entry	Compound	λ_max^a/nm	ε^a/(L•mol^－1•cm^－1)	E_HOMO^b/eV	E_LUMO^b/eV
1	87a ([3]CP)	409	2.4×10⁵	－5.0	－2.4
2	87b ([4]CP)	414	3.0×10⁵	－5.0	－2.5
3	87c ([5]CP)	423	4.4×10⁵	－5.0	－2.4
4	89a ([3]CPB)	435	2.8×10⁵	－5.0	－2.3
5	89b ([4]CPB)	430	4.3×10⁵	－5.1	－2.3
6	89c ([5]CPB)	428	7.5×10⁵	－5.1	－2.2
7	89d ([6]CPB)	427	1.2×10⁵	－5.1	－2.2

表3. 含卟啉共轭纳米环[n]CP和[n]CPB的光电性质对比

Table 3. Comparison of the optoelectronic properties of [n]CP and [n]CPB

图15. 含PDI单元共轭纳米环的合成[62-63,65-66]

Figure 15. Synthesis of PDI-based conjugated nanohoops

图16. 柱状纳米环设计思路

Figure 16. Design principles for columnar conjugated nanotubes

图17. (a)共轭纳米环[4]C-NDTI的合成与(b) 105-A4单晶结构及堆积模式[24]

Figure 17. Synthesis of [4]C-NDTI, and (b) crystal structure and 2D packing mode of 105-A4

图18. [4]C-NDTI的6个异构体[24](A和B分别代表NDTI单元的两种不同朝向)

Figure 18. Six possible isomers of [4]C-NDTI (the orientation of the NDTI units marked as A and B with different color, respectively)

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