Acceleration of the Diels-Alder Reaction between 9-Functionalized Anthracenes and C60/C70 in the Cavity of a Water Soluble Subphthalocyanine Cage

被引：3

作者：

Salazar, Ainhoa ^{[1
]}

Labella, Jorge ^{[1
]}

Kumar, Sunit ^{[1
]}

Torres, Tomas ^{[1
,2
,3
]}

de la Torre, Gema ^{[1
,2
]}

机构：

[1] Univ Autonoma Madrid, Dept Organ Chem, Campus Cantoblanco C Francisco Tomas Y Valiente 7, Madrid 28049, Spain

[2] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Campus Cantoblanco, Madrid 28049, Spain

[3] Inst Madrileno Estudios Avanzados IMDEA Nanocienci, Campus Cantoblanco, Madrid 28049, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 04期

关键词：

subphthalocyanine; metallo-organic cage; catalysis; water; fullerene; CYCLOADDITIONS; FUNCTIONALIZATION; NANOSPHERES; CHEMISTRY; CATALYSIS; ADDUCTS; C-70;

D O I：

10.1002/adsc.202301336

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein we report on the acceleration of the Diels-Alder reaction between a series of 9-functionalized anthracenes and C-60/C-70 encapsulated in a water-soluble metallo-organic Pd(II)-subphthalocyanine cage (SubPc-cage), which performs as a catalytic molecular reactor that provides a beneficial hydrophobic environment. Negatively and positively charged anthracenes do not react either with C-60 or C-70, due to a favored solvation in water medium and/or to detrimental interactions with positively-charged Pd(II) corners of SubPc-cage. Experiments with C-60 and C-70 rendered parallel results, although C-70 proved more reactive, leading to anthracene cycloadducts by reaction in the alpha bonds. All the results have been rationalized by theoretical calculations at the GFN2-xTB level.

引用

页码：934 / 941

页数：8