磺酰基杯[4]芳烃基配位分子笼的催化应用★

doi:10.6023/A26060209

摘要/Abstract

超分子催化旨在模拟天然酶的高效与特异性, 配位分子笼因其可编程的纳米空腔而成为这一领域最有活力和发展前途的方向之一. 硫代杯[4]芳烃及其氧化衍生物磺酰基杯[4]芳烃作为一类具有独特锥形构象和多配位点的“预组织”大环配体, 能够与过渡金属离子组装形成结构明确、稳定性优异的多核簇次级构筑单元. 基于“硫代/磺酰基杯[4]芳烃-金属簇”结构基元, 结合不同的多羧酸桥联配体, 已成功构筑了一系列拓扑丰富、尺寸可调的配位分子笼. 借助于该类配位超分子体系, 发展出多种催化功能化策略, 包括利用空腔限域效应、在骨架上引入活性位点以及封装金属纳米颗粒等, 成功实现了从简单模型反应到不对称合成、光/电催化及串联反应等复杂化学转化. 系统总结了基于硫代/磺酰基杯[4]芳烃的配位分子笼在催化领域的最新研究进展, 着重分析了该领域从“依赖空腔物理限域”向“理性设计协同催化”的范式演进过程, 并特别强调了赋予催化选择性和效率的设计思路与设计原理, 并为该领域未来的发展方向提供了展望.

关键词: 配位分子笼, 磺酰基杯[4]芳烃, 超分子催化, 协同催化

Supramolecular catalysis aims to mimic the high efficiency and specificity of natural enzymes, and coordination cages have emerged as one of the most active and promising directions in this field due to their tunable nano-cavities. Thiacalix[4]arenes and their oxidized derivatives, sulfonylcalix[4]arenes, are a class of “preorganized” macrocyclic ligands with a unique cone conformation and multiple coordination sites. They can assemble with transition metal ions to form well-defined, highly stable polynuclear cluster secondary building units (SBUs). Based on this “thia-/sulfonyl-calix[4]arene-metal cluster” motif and employing various polycarboxylate bridging linkers, various coordination cages with diverse topologies and tunable dimensions have been successfully constructed. By virtue of this type of coordination supramolecular cages, researchers have developed several catalytic functionalization strategies, including exploiting the cavity confinement effect, introducing active sites into the cage backbone, and encapsulating catalytic guest species. These strategies have enabled a wide range of complex chemical transformations, from simple model reactions to asymmetric synthesis, photo/electrocatalysis, and cascade reactions. This review systematically summarizes the latest research progress on thia-/sulfonyl-calix[4]arene-based coordination cages in catalysis. It specifically analyzes the paradigm shift in this field from “relying on mere physical confinement” toward “rationally designed cooperative catalysis,” with a particular emphasis on the design principles underlying enhanced catalytic selectivity and efficiency. Finally, the review provides perspectives on future directions for this field.

Key words: coordination cages, sulfonylcalix[4]arenes, supramolecular catalysis, cooperative catalysis

引用此文

戴枫荣, 陈忠宁. 磺酰基杯[4]芳烃基配位分子笼的催化应用^★[J]. 化学学报, 2026, 84(8): 1343-1354.

Fengrong Dai, Zhongning Chen. Catalytic Applications of Sulfonylcalix[4]arene-Based Coordination Cages^★[J]. Acta Chimica Sinica, 2026, 84(8): 1343-1354.

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图/表 10

图1. 通过多羧酸配体的设计实现磺酰基杯[4]芳烃基配位分子笼的结构调控. 经参考文献[28]许可转载, 版权2024, 作者

Figure 1. Structural regulation of sulfonylcalix[4]arene-based coordination cages by judicious design of various carboxylate linkers. Reprinted with permission from ref. [28], Copyright 2024 The Authors

催化体系	催化活性中心来源	核心结构/策略	催化应用	关键性能指标	文献
MOSC-1, MOSC-2	金属簇节点: Brønsted酸性μ₄-H₂O	空腔限域静电别构调控	Knoevenagel缩合	底物选择性: 1-芘甲醛, 产率67% vs 2-萘甲醛, 产率5%	[35-36]
1-Co, 1-Ni	金属簇节点: M₄TBSC, M=Co, Ni; 配体功能化: 吡啶鎓功能化	骨架离子化静电微环境调控	电化学析氧反应(OER)	过电位: 0.290 V @10 mA•cm^-2 (1-Co); Tafel斜率: 75 mV•dec^-1; 稳定性: 48 h连续电解无显著衰减	[37]
Cu₄TBSC基分子笼	金属簇节点: 配位不饱和Cu(II)位点)	结构缺陷开放金属位点	伯醇选择性氧化(醇→羧酸)	底物选择性: 4-甲氧基苄醇99%产率(4 h)、4-硝基苄醇仅得19%羧酸＋74%醛(中间体); 循环性: 4次循环后活性保持>90%	[38]
{M₂₀V₈} (M=Fe, Co, Ni)方锥纳米笼	金属簇节点: M₂₀V₈簇	金属替换能带调控	可见光光热催化硫醚氧化脱硫	光热转换效率: Fe₂₀V₈ 85.87%; 催化转化率: Fe₂₀V₈>99%; 性能排序: Fe₂₀V₈>>Co₂₀V₈>Ni₂₀V₈	[39]
Co-PYDC	金属簇节点: 开放Co(II)位点＋Brønsted酸性μ₃-H₂O	缺陷工程双活性区域(外腔/内腔)	串联催化: 烯烃→β-氨基醇	一锅法转化率: 苯乙烯衍生物) 96%; 区域选择性: 仅生成β-位开环产物	[40]
延长型八面体笼	配体功能化: -CH₂NH- Brønsted碱金属簇节点: Brønsted酸性μ₄-H₂O	几何操纵(空腔拉伸) 酸碱双功能协同	Knoevenagel缩合	底物1-芘甲醛, 产率89%	[43]
手性Mn(salen)笼	配体功能化: 手性Mn(salen)活性中心	骨架隔离空腔限域	氧化动力学拆分 (仲醇)/烯烃环氧化	对映选择性(ee): 1-苯乙醇>99% (拆分产物); 选择性因子(krel): 最高35.0 (vs游离Mn(salen) 10.3~26.9);	[44]
ImBDC-Co, ImBDC-Ni	配体功能化: 咪唑鎓Lewis酸/卤素抗衡离子	离子型功能化配体均相/异相结合	CO₂环加成反应	产物选择性:>99% (环氧氯丙烷); 底物范围: 脂肪族环氧化物产率>97%, 芳香族环氧化物>80%; 循环性: 3次循环无明显活性损失	[45]
蒽醌基光催化笼	配体功能化: 蒽醌光敏剂	光活性骨架空腔预组织	光催化[2＋2]环加成(查尔酮)	非对映选择性(dr): syn-HH∶anti-HT=13∶1; 转化率: 96% (12 h)	[46]
PCC-15/16/17	配体功能化: -NH₂- Brønsted碱) 金属簇节点: Brønsted酸性μ₄-H₂O	活性位点间距精确调控: 调节-NH₂-与μ₄-H₂O距离(从5.6 Å至12.4 Å)	Knoevenagel缩合	间距-活性关系: PCC-17 (5.6 Å) 96%产率>PCC-16 (12.4 Å) 21% 产率>PCC-15 (无-NH₂)<5%产率; 底物范围: 多种芳香醛产率>95%	[47]
Pt@CIAC-121	封装客体: Pt纳米簇	S-锚点(化学) 空腔限域(物理)	电解水析氢反应(HER)	起始电位: -0.24 V (vs Ag/AgCl, 略正于Pt/C); 电流密度: 在-0.60 V时, Pt@CIAC-121为 20 mA•cm^-2•µg^-1 (Pt/C的2倍)	[50]
Ru NPs@PCC-2a	封装客体: Ru纳米颗粒	高负电荷笼(-30) 静电排斥/空间限域	氨硼烷甲醇解脱氢	TOF: 304.4 min^-1 (当时金属基催化剂最高值); 反应时间: 4.5 min内完成[n(H₂)∶n(AB)=3.0∶1]	[51]
Co NCs@PCC-2a, Co NCs@PCC-2b	封装客体: Co 纳米簇	高负电荷笼(-30, PCC-2a) vs 低负电荷笼(-6, PCC-2b) (对比论证电荷效应关键作用)	氨硼烷水解	TOF (PCC-2a): 90.1 min^-1 (第一过渡系金属最高); TOF (PCC-2b): 22.5 min^-1 (严重聚集)	[52]
Ru(bpy)₃@PCC-2a	封装客体(Ru(bpy)₃^2＋分子催化剂	共封装(催化剂＋底物)	光催化降解亚甲基蓝(MB)	降解率(4 h): 94.9% (Ru(bpy)₃@PCC-2a) vs 19.8% (游离Ru(bpy)₃^2＋); 循环性: 5次循环后活性保持>90%	[53]

催化体系	催化活性中心来源	核心结构/策略	催化应用	关键性能指标	文献
MOSC-1, MOSC-2	金属簇节点: Brønsted酸性μ₄-H₂O	空腔限域静电别构调控	Knoevenagel缩合	底物选择性: 1-芘甲醛, 产率67% vs 2-萘甲醛, 产率5%	[35-36]
1-Co, 1-Ni	金属簇节点: M₄TBSC, M=Co, Ni; 配体功能化: 吡啶鎓功能化	骨架离子化静电微环境调控	电化学析氧反应(OER)	过电位: 0.290 V @10 mA•cm^-2 (1-Co); Tafel斜率: 75 mV•dec^-1; 稳定性: 48 h连续电解无显著衰减	[37]
Cu₄TBSC基分子笼	金属簇节点: 配位不饱和Cu(II)位点)	结构缺陷开放金属位点	伯醇选择性氧化(醇→羧酸)	底物选择性: 4-甲氧基苄醇99%产率(4 h)、4-硝基苄醇仅得19%羧酸＋74%醛(中间体); 循环性: 4次循环后活性保持>90%	[38]
{M₂₀V₈} (M=Fe, Co, Ni)方锥纳米笼	金属簇节点: M₂₀V₈簇	金属替换能带调控	可见光光热催化硫醚氧化脱硫	光热转换效率: Fe₂₀V₈ 85.87%; 催化转化率: Fe₂₀V₈>99%; 性能排序: Fe₂₀V₈>>Co₂₀V₈>Ni₂₀V₈	[39]
Co-PYDC	金属簇节点: 开放Co(II)位点＋Brønsted酸性μ₃-H₂O	缺陷工程双活性区域(外腔/内腔)	串联催化: 烯烃→β-氨基醇	一锅法转化率: 苯乙烯衍生物) 96%; 区域选择性: 仅生成β-位开环产物	[40]
延长型八面体笼	配体功能化: -CH₂NH- Brønsted碱金属簇节点: Brønsted酸性μ₄-H₂O	几何操纵(空腔拉伸) 酸碱双功能协同	Knoevenagel缩合	底物1-芘甲醛, 产率89%	[43]
手性Mn(salen)笼	配体功能化: 手性Mn(salen)活性中心	骨架隔离空腔限域	氧化动力学拆分 (仲醇)/烯烃环氧化	对映选择性(ee): 1-苯乙醇>99% (拆分产物); 选择性因子(krel): 最高35.0 (vs游离Mn(salen) 10.3~26.9);	[44]
ImBDC-Co, ImBDC-Ni	配体功能化: 咪唑鎓Lewis酸/卤素抗衡离子	离子型功能化配体均相/异相结合	CO₂环加成反应	产物选择性:>99% (环氧氯丙烷); 底物范围: 脂肪族环氧化物产率>97%, 芳香族环氧化物>80%; 循环性: 3次循环无明显活性损失	[45]
蒽醌基光催化笼	配体功能化: 蒽醌光敏剂	光活性骨架空腔预组织	光催化[2＋2]环加成(查尔酮)	非对映选择性(dr): syn-HH∶anti-HT=13∶1; 转化率: 96% (12 h)	[46]
PCC-15/16/17	配体功能化: -NH₂- Brønsted碱) 金属簇节点: Brønsted酸性μ₄-H₂O	活性位点间距精确调控: 调节-NH₂-与μ₄-H₂O距离(从5.6 Å至12.4 Å)	Knoevenagel缩合	间距-活性关系: PCC-17 (5.6 Å) 96%产率>PCC-16 (12.4 Å) 21% 产率>PCC-15 (无-NH₂)<5%产率; 底物范围: 多种芳香醛产率>95%	[47]
Pt@CIAC-121	封装客体: Pt纳米簇	S-锚点(化学) 空腔限域(物理)	电解水析氢反应(HER)	起始电位: -0.24 V (vs Ag/AgCl, 略正于Pt/C); 电流密度: 在-0.60 V时, Pt@CIAC-121为 20 mA•cm^-2•µg^-1 (Pt/C的2倍)	[50]
Ru NPs@PCC-2a	封装客体: Ru纳米颗粒	高负电荷笼(-30) 静电排斥/空间限域	氨硼烷甲醇解脱氢	TOF: 304.4 min^-1 (当时金属基催化剂最高值); 反应时间: 4.5 min内完成[n(H₂)∶n(AB)=3.0∶1]	[51]
Co NCs@PCC-2a, Co NCs@PCC-2b	封装客体: Co 纳米簇	高负电荷笼(-30, PCC-2a) vs 低负电荷笼(-6, PCC-2b) (对比论证电荷效应关键作用)	氨硼烷水解	TOF (PCC-2a): 90.1 min^-1 (第一过渡系金属最高); TOF (PCC-2b): 22.5 min^-1 (严重聚集)	[52]
Ru(bpy)₃@PCC-2a	封装客体(Ru(bpy)₃^2＋分子催化剂	共封装(催化剂＋底物)	光催化降解亚甲基蓝(MB)	降解率(4 h): 94.9% (Ru(bpy)₃@PCC-2a) vs 19.8% (游离Ru(bpy)₃^2＋); 循环性: 5次循环后活性保持>90%	[53]

表1. 基于磺酰基杯[4]芳烃的配位分子笼代表性催化性能对比

Table 1. Comprehensive comparison of representative catalytic performance of sulfonylcalix[4]arene-based coordination cages

表1. 基于磺酰基杯[4]芳烃的配位分子笼代表性催化性能对比

Table 1. Comprehensive comparison of representative catalytic performance of sulfonylcalix[4]arene-based coordination cages

图2. 配位分子笼催化的Knoevenagel缩合反应. 经参考文献[35]许可转载, 版权2016, Wiley-VCH

图3. M20V8 (M=Fe、Co、Ni)配位分子笼的合成及四方锥结构示意图: (a) H4TC4A配体与M4-TC4A次级构筑单元(PSBUs); (b)和(c) M20V8配位分子笼的分子结构示意图; (d) M20V8配位分子笼的十六元环窗口示意图; (e)五个M4-TC4A次级构筑单元与八个{VO4}基团的排布方式. 经参考文献[39]许可转载, 版权2025, Royal Society of Chemistry

Figure 3. Schematic illustration of the synthesis and square pyramid structure of the M20V8 (M=Fe, Co, and Ni) cages. (a) The H4TC4A ligand and the M4-TC4A PSBUs. (b) and (c) Representation of the molecular structure of the M20V8 cages. (d) Illustration of the 16-membered ring window of the M20V8 cages. (e) Arrangement of five M4-TC4A PSBUs and eight {VO4} groups. Reprinted with permission from ref. [39], Copyright 2025 Royal Society of Chemistry

图4. 配位分子笼Co-PYDC的(a)自组装过程和(b)催化串联反应合成β-氨基醇的反应机理. 经参考文献[40]许可转载, 版权2026, Springer Nature

Figure 4. (a) Self-assembly of the coordination cage Co-PYDC; (b) Proposed mechanism for the synthesis of β-amino alcohols through tandem reactions catalyzed by cage Co-PYDC. Reprinted with permission from ref. [40], Copyright 2026 Springer Nature

图5. (a)具有畸变八面体结构的配位分子笼设计; 经参考文献[43]许可转载, 版权2022, 作者; (b)手性Mn(salen)修饰的配位分子笼单晶结构示意图. 经参考文献[44]许可转载, 版权2018, Wiley-VCH

Figure 5. (a) Design of coordination cage with distorted octahedral structures; Reprinted with permission from ref. [43], Copyright 2022 The Authors; (b) Single-crystal X-ray structure of the chiral Mn(salen)-functionalized coordination cage. Reprinted with permission from ref. [44], Copyright 2018 Wiley-VCH

图6. (a)咪唑鎓功能化和(b)蒽醌功能化配位分子笼的设计和合成. 经参考文献[45,46]许可转载, 版权2021, Royal Society of Chemistry

Figure 6. Design and synthesis of (a) imidazolium-functionalized and (b) anthraquinone-functionalized coordination cages. Reprinted with permission from ref. [45,46], Copyright 2021 Royal Society of Chemistry

图7. 通过配体工程精确调控活性位点间距的电性同构三棱柱状配位分子笼(PCC-15、PCC-16、PCC-17)的合成. 经参考文献[47]许可转载, 版权2026, 作者

Figure 7. Synthesis of electrically isostructural trigonal-prismatic PCCs (PCC-15, PCC-16, PCC-17) with precisely tuned interactive site distances via ligand engineering. Reprinted with permission from ref. [47], Copyright 2026 The Authors

图8. 三棱柱配位分子笼(CIAC-121)的自组装及超细Pt纳米簇的制备. 经参考文献[50]许可转载, 版权2016, American Chemical Society

Figure 8. The assembly of trigonal prismatic coordination cage (CIAC-121) and the fabrication of ultrafine Pt NCs. Reprinted with permission from ref. [50], Copyright 2016 American Chemical Society

图9. 配位分子笼封装(a)钌和(b)钴纳米粒子用于氨硼烷催化水解反应. 经参考文献[51]许可转载, 版权2018, 作者; 参考文献[52]许可转载, 版权2018, Wiley-VCH

Figure 9. Coordination cages encapsulate (a) Ru and (b) Co nanoparticles for the catalytic reaction of hydrolysis of ammonia borane. Reprinted with permission from ref. [51], Copyright 2018 The Authors and ref. [52], Copyright 2018 Wiley-VCH

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