Organic co-crystals of 1,3-bis(4-pyridyl)azulene with a series of hydrogen-bond donors

Abstract

1,3-Bis(4-pyridyl)azulene has been employed as a hydrogen bond acceptor to construct two-component organic cocrystals.

Halogen bonded supramolecular assemblies constructed from azulene derivatives and perfluorinated di-/triiodobenzenes

“…While, the crystal structure of 1,3-bis(4-pyridyl)azulene, 2 , has been previously described by us, 38 the 1,3-azulendicarboxaldehyde, 1 , has not crystallographically described until now. Suitable crystals for X-ray diffraction were obtained by slow evaporation of chloroform solution.…”

“…We have previously shown the ability of the 1,3-bis(4-pyridyl)azulene to function as hydrogen bond acceptor with various di- and tri-topic hydrogen-bond donors. 38 We recall the self-assembled 3D architecture formed with 1,3,5-benzenetricarboxylic acid (trimesic acid), consisting of helical chains of trigonal building block connected by this bent azbbpy, unlike the two-dimensional honeycomb networks formed by linear 4,4′-bipyridine, 62 or trihelix motif found in binary co-crystal of bent 2,5-bis(4-pyridyl)-1,3,4-oxadiazole. 63 We have shown that, subtle variations in the molecular structure of the building-blocks has a strong impact on the supramolecular arrangements.…”

“…As halogen bond acceptor, we have chosen two types of 1,3-substituted azulene derivatives, which differ in electronic properties, size and shape, namely 1,3-azulenedicarboxaldehyde (azdicho), 1 and 1,3-bis(4-pyridyl) azulene (azbbpy), 2 (Scheme 1). While, 1,3-bis(4-pyridyl)azulene has been recently incorporated by us in the construction of various hydrogen bonded co-crystals or crystalline coordination polymers, [38][39][40] the 1,3-azulenedicarboxaldehyde has not been used in the construction of non-covalent supramolecular assemblies, its relevant role in crystal engineering being outlined recently by Zhao et al in the development of redox active covalent-organic framework for organic memristors. 41 It should be mentioned that azulene is an intriguing molecule with intrinsic bipolar structure, possessing anomalous fluorescence and redox properties.…”

Azulene‐Based Molecules, Polymers, and Frameworks for Optoelectronic and Energy Applications

“…synthesized a new binary molecular cocrystal and salt through the supramolecular interaction between 1,3‐bis(4‐pyridyl)azulene (azbbpy) and various aromatic hydrogen bond donors. [ 125 ] As displayed in Figure , azbbpy can self‐assemble through hydrogen bonding to form a supramolecular structure. In the study of Ion et al., a 2D supramolecular network was generated using a 1:1 mixture of the binary cocrystal of azbbpy and 4,4′‐biphenol(biphenol).…”

Design, Synthesis, and Biological Evaluation of New Azulene-Containing Chalcones

“…In contrast to common benzene and naphthalene aromatic units, azulene is a non-benzenoid aromatic system with unusual properties and beautiful blue color owing to intrinsic bipolar structure [ 13 ]. Azulene derivatives have attracted the interest of many research groups due to their applications in molecular switchers [ 12 ], organic transistors (FETs) [ 14 ], light-emitting diodes (LEDs) [ 15 ], supramolecular materials [ 16 , 17 ], or optical data storage devices [ 18 , 19 ]. Although azulenes are known for their biological activity in natural plant extracts [ 20 ], dopamine receptors [ 21 ], or inhibition of histamine release from mast-cell-like cells in the stomach [ 22 ], this scaffold has never been used as a pharmacophoric element in the design of biologically active chalcones.…”