Shape-Persistent Tetrahedral [4+6] Boronic Ester Cages with Different Degrees of Fluoride Substitution

Sven M Elbert; Nicolas I Regenauer; Dorothee Schindler; Wen-Shan Zhang; Frank Rominger; Rasmus R Schröder; Michael Mastalerz

doi:10.1002/chem.201802123

Shape-Persistent Tetrahedral [4+6] Boronic Ester Cages with Different Degrees of Fluoride Substitution

Chemistry. 2018 Aug 6;24(44):11438-11443. doi: 10.1002/chem.201802123. Epub 2018 Jul 6.

Authors

Sven M Elbert¹, Nicolas I Regenauer¹, Dorothee Schindler¹, Wen-Shan Zhang², Frank Rominger¹, Rasmus R Schröder², Michael Mastalerz^{1

2}

Affiliations

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
² Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

PMID: 29897652
DOI: 10.1002/chem.201802123

Abstract

In recent years the interest of shape-persistent organic cage compounds synthesized by dynamic covalent chemistry (DCC) has risen, because these cages are potentially interesting for gas sorption or -separation. One such reaction in DCC is the condensation of boronic acids with diols to form boronic esters. Most interestingly, the variety of geometries and sizes for boronic ester cages is much lower than that of, for example, imine-based cages. Here, a small series of shape-persistent [4+6] tetrahedral boronic ester cages is introduced. One cage has a high specific surface area of 511 m² g^-1 and selectively adsorbs ethane over ethylene and acetylene.

Keywords: boronic ester; crystal structures; fluoride; halogen bonds; organic cage compounds.