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heterogeneous catalysts with programmable topologies generated by reticulation of organocatalysts into metal-organic frameworks:The case of squaramide

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Nano Research 2021年第2期14卷 458-465页

作者： Anna Broto-Ribas Claudia Vignatti Alicia Jimenez-Almarza Javier Luis-Barrera Zahra Dolatkhah Felipe Gandara Inhar Imaz Ruben Mas-Balleste Jose Aleman Daniel Maspoch Catalan Institute of Nanoscience and Nanotechnology(ICN2) CSIC and The Barcelona Institute of Science and Technology08193 BarcelonaSpain Inorganic Chemistry Department Modulo 7Universidad Autonoma de Madrid28049 MadridSpain Organic Chemistry Department Modulo 1Universidad Autonoma de Madrid28049 MadridSpain Materials Science Factory Instituto de Ciencia de Materiales de Madrid(ICMM)Consejo Superior de Investigaciones Cientificas(CSIC)Calle Sor Juana Ines de la Cruz328049 MadridSpain Institute for Advanced Research in Chemical Sciences(IAdChem) Campus Universidad Autonoma de Madrid28049 MadridSpain Institucio Catalana de Recerca i Estudis Avangats(ICREA) 08100 BarcelonaSpain

A well-established strategy to synthesize heterogeneous,metal-organic framework(MOF)catalysts that exhibit nanoconfinement effects,and specific pores with highly-localized catalytic sites,is to use organic linkers containing organocatalytic centers.here,we report that by combining this linker approach with reticular chemistry,and exploiting three-dimensioanl(3D)MOF-structural data from the Cambridge Structural Database,we have designed four heterogeneous MOF-based catalysts for standard organic transformations.These programmable MOFs are isoreticular versions of pcu IRMOF-16,feu UiO-68 and pillared-pcu SNU-8X,the three most common topologies of MOFs built from the organic linker p.p'-terphenyldicarboxylic acid(tpdc).To synthesize the four squaramide-based MOFs,we designed and synthesized a linker,4,4’-((3,4-dioxocyclobut-1-ene-1,2-diyl)bis(azanedyil))dibenzoic acid(Sq_tpdc),which is identical in directionality and length to tpdc but which contains organocatalytic squaramide centers.Squaramides were chosen because their immobilization into a framework enhances its reactivity and stability while avoiding any self-quenching phenomena.Therefore,the four MOFs share the same organocatalytic squaramide moiety,but confine it within distinct pore environments.We then evaluated these MOFs as heterogeneous h-bonding catalysts in organic transformations:a Friedel-Crafts alkylation and an epoxide ring-opening.Some of them exhibited good performance in both reactions but all showed distinct catalytic profiles that reflect their structural differences.

关键词： reticular chemistry metal-organic frameworks h-bond catalysis squaramide Friedel-Cratts epoxide ring-opening

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