Phenol Derivatives as Co-Crystallized Templates to Modulate Trimesic-Acid-Based Hydrogen-Bonded Organic Molecular Frameworks

Guangchuan Ou,Qiong Wang,Xiaofeng Wang,Qiang Zhou

doi:10.3390/cryst11040409

Guangchuan Ou, Qiong Wang + Show 2 more

Open Access

https://doi.org/10.3390/cryst11040409

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Abstract

Five host−guest trimesic-acid-based hydrogen-bonds framework compounds with different guests, namely [(TMA)4·(TMB)3] (1), [(TMA)2·(DMB)1.5] (2), [(TMA)6·(MP)] (3), [(TMA)·(EP)] (4) and [(TMA)·(PP)] (5) (TMA = trimesic acid, TMB = 1,3,5-trimethoxybenzene, DMB = 1,4-dimethoxybenzene, MP = 4-methoxyphenol, EP = 4-ethoxyphenol and PP = 4-propoxyphenol), were obtained through co-crystallization, and were characterized by elemental analysis, infrared spectroscopy analysis, and thermogravimetric analysis. The trimesic acid molecules comprise a hydrogen bonding six-membered cyclic host network that is found in a two-dimensional arrangement in compounds 1 and 2, and in a nine-fold interpenetrated three-dimensional structure in compound 3. In compounds 4 and 5, the trimesic acid and EP/PP molecules form a hydrogen-bonded six-membered cyclic network, resulting in a one-dimensional chain structure through O−H…O hydrogen bonds.

Highlights

The design and assembly of hydrogen-bonded organic frameworks (HOFs) or supramolecular-organic frameworks (SOFs) has attracted intense interest because of the great potential of these frameworks in many materials science and solid-state applications [1,2,3,4,5,6,7,8,9]
Among the various components use in hydrogen-bonded assemblies, multi-carboxylates have been used in numerous HOFs due to the wide variety of their spacers and angles
The crystal structure of the α-polymorph displays the infinite hydrogen-bonded chicken-wire network formed by R22(8) dimerization of carboxylic acid groups

Summary

Introduction

The design and assembly of hydrogen-bonded organic frameworks (HOFs) or supramolecular-organic frameworks (SOFs) has attracted intense interest because of the great potential of these frameworks in many materials science and solid-state applications [1,2,3,4,5,6,7,8,9]. Trimesic acid (TMA) with the α-polymorph structure with three carboxylate groups was first reported in 1969 [10] and is still an important building block for the construction of HOFs or SOFs due to its predictable honeycomb crystal lattice structure formation [11,12,13]. The crystal structure of the α-polymorph displays the infinite hydrogen-bonded chicken-wire network formed by R22(8) dimerization of carboxylic acid groups. No universal chaperones co-crystallizing with various small molecule [20] such as porphyrins, calixarenes or cyclodextrins with a proven ability to obtain the structure of a broad range of different organic molecules have been reported [21,22,23,24,25,26,27,28]. IR (KBr): 3075 (w), 2929 (w), 1721 (s), 1606 (m), 1510 (m), 1402 (m), 1278 (m), 1108 (m), 936 (m), 830 (m), 742 (s), 686 (s), 519 (s) cm−1

Crystal Structure Determination

Results and Discussion

Thermogravimetric Analysis

Conclusions