e-journal

Crystals as Molecules: Postsynthesis Covalent Functionalization of Zeolitic Imidazolate Frameworks

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The ability to covalently functionalize molecules is a long standing practice in organic chemistry that has led to advances in the synthesis of natural products, pharmaceuticals, and polymers. However, the analogous chemistry of crystalline extended solids remains undeveloped because they generally lose their structural
integrity under the reaction conditions required to carry out meaningful organic transformations. Recent reports showed the viability of functionalizing the organic links of porous metal-organic frameworks using mild organic reactions. Here, we extend this strategy to zeolitic imidazolate frameworks (ZIFs), which have
unusual thermal and chemical stability, and thus are ideal platforms for performing useful organic transformations under strong reaction conditions. Specifically, the imidazolate-2-carboxyaldehyde (ICA)
links, which join tetrahedral zinc(II) centers in a new porous ZIF (vide infra), have been reduced by NaBH4 to the corresponding alcohol derivative, and converted to an imine functionality in refluxing methanol (Scheme 1). Despite these strong reaction conditions, the integrity of the ZIF structure and its crystallinity are maintained throughout the synthesis. The isolated ZIF derivatives indicate that those organic reactions proceeded in high conversions. In essence the success in achieving typical organic
reactions in crystals of extended structures like ZIFs makes the idea of using the “crystal as a molecule” a reality and opens many opportunities for employing the arsenal of organic reactions in the covalent functionalization of extended structures.

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Informasi Detail

Judul Seri

J. AM. CHEM. SOC.

No. Panggil

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Penerbit

New York : American Chemical Society., 2008

Deskripsi Fisik

J. AM. CHEM. SOC. 2008, 130, 12626–12627

Bahasa

English

ISBN/ISSN

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Klasifikasi

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Tipe Isi

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Tipe Media

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Tipe Pembawa

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Edisi

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Subjek

KIMIA

Info Detail Spesifik

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Pernyataan Tanggungjawab

agus

Versi lain/terkait

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