Self-Assembly of Fluorinated Boronic Esters and 4,4′-Bipyridine into 2:1 N→B Adducts and Inclusion of Aromatic Guest Molecules in the Solid State: Application for the Separation of o,m,p‑Xylene

Gonzalo Campillo-Alvarado; Eva C Vargas-Olvera; Herbert Höpfl; Angel D Herrera-España; Obdulia Sánchez-Guadarrama; Hugo Morales-Rojas; Leonard R MacGillivray; Braulio Rodríguez-Molina; Norberto Farfán

doi:10.1021/acs.cgd.7b01368

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Self-Assembly of Fluorinated Boronic Esters and 4,4′-Bipyridine into 2:1 N→B Adducts and Inclusion of Aromatic Guest Molecules in the Solid State: Application for the Separation of o,m,p‑Xylene

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Self-Assembly of Fluorinated Boronic Esters and 4,4′-Bipyridine into 2:1 N→B Adducts and Inclusion of Aromatic Guest Molecules in the Solid State: Application for the Separation of o,m,p‑Xylene

Gonzalo Campillo-Alvarado, Eva C Vargas-Olvera, Herbert Höpfl, Angel D Herrera-España, Obdulia Sánchez-Guadarrama, Hugo Morales-Rojas, Leonard R MacGillivray, Braulio Rodríguez-Molina and Norberto Farfán

Crystal growth & design, Vol.18(5), pp.2726-2743

05/02/2018

DOI: 10.1021/acs.cgd.7b01368

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Abstract

A series of 2:1 fluorinated arylboronic ester adducts with 4,4′-bipyridine sustained by N→B dative bonds have been synthesized. The degree of fluorination in the arylboronic esters derived from catechol is shown to modulate the molecular conformation of the coordinated boronic ester moieties and the intermolecular interactions by means of C–H···F and F···F contacts that sustain the crystal lattices. The adduct derived from the catechol ester of 2,4-difluorophenylboronic acid was chosen to examine the formation of inclusion complexes with a large number of aromatic guests, affording solvates, cocrystals, and a cocrystal solvate. Six different crystal structure types with 1:1, 1:2, and 1:2:2 N→B adduct–guest ratios were observed, whose supramolecular organization is strongly influenced by the formation of sandwich-type complexes between the host and guest molecules. The host–guest interactions involve π···π interactions with the bipyridine linkers and additional contacts with the catecholate and B-arylF substituents, indicating a large flexibility of the N→B adducts to adapt to the guest stereochemistry. The versatility of the crystallization system was employed to isolate o-xylene from an equimolar mixture of o-, m-, and p-xylene.

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Title: Subtitle: Self-Assembly of Fluorinated Boronic Esters and 4,4′-Bipyridine into 2:1 N→B Adducts and Inclusion of Aromatic Guest Molecules in the Solid State: Application for the Separation of o,m,p‑Xylene
Creators: Gonzalo Campillo-Alvarado - Department of Chemistry
Eva C Vargas-Olvera - Universidad Autónoma del Estado de Morelos
Herbert Höpfl - Universidad Autónoma del Estado de Morelos
Angel D Herrera-España - Universidad Autónoma del Estado de Morelos
Obdulia Sánchez-Guadarrama - Universidad Autónoma del Estado de Morelos
Hugo Morales-Rojas - Universidad Autónoma del Estado de Morelos
Leonard R MacGillivray - Department of Chemistry
Braulio Rodríguez-Molina
Norberto Farfán
Resource Type: Journal article
Publication Details: Crystal growth & design, Vol.18(5), pp.2726-2743
Publisher: American Chemical Society
DOI: 10.1021/acs.cgd.7b01368
ISSN: 1528-7483
eISSN: 1528-7505
Grant note: DOI: 10.13039/100010096, name: Secretar?a de Educaci?n P?blica; DOI: 10.13039/501100003141, name: Consejo Nacional de Ciencia y Tecnolog?a, award: 132227, 281251, 229929
Language: English
Date published: 05/02/2018
Academic Unit: Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
Record Identifier: 9984216585602771

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