article · Crystal Growth & Design
Researchers have developed a simple and efficient synthetic method to produce four new diaminotriazinyl-functionalised oligopyridine mimics in yields exceeding 90 percent. Designed as structural analogues of standard oligopyridines, these molecules replace specific pyridine rings with diaminotriazinyl groups that introduce complementary hydrogen-bond donor and acceptor sites. Detailed physical, spectroscopic, and crystallographic analysis revealed that these groups direct predictable solid-state self-assembly through hydrogen bonding. Depending on the molecular geometry, the compounds assemble into diverse structural forms including discrete dimers, two-dimensional networks, bilayers, and ribbons. By altering the number of diaminotriazinyl units, researchers can fine-tune molecular geometry and solid-state packing. Additionally, computational docking studies demonstrate that these multifunctional building blocks interact favourably with DNA and enzyme targets, highlighting their potential utility in supramolecular chemistry and biological recognition.
Controlling how molecules assemble in the solid state is vital for engineering new materials with tailored functions. By combining metal-binding sites with predictable hydrogen-bonding units, these new chemical building blocks enable more reliable design of complex architectures. Their demonstrated ability to interact with biological targets such as enzymes and DNA opens possibilities for future applications in bio-inspired chemistry.
This work represents early-stage fundamental chemistry. The compounds could serve as versatile functional building blocks for researchers developing advanced coordination materials, sensors, or pharmaceutical agents targeting DNA and enzymes. However, practical commercial applications remain distant, as the current findings are restricted to chemical synthesis, solid-state structural characterisation, and preliminary in silico docking studies.
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Abstract The design of molecular tectoligands capable of combining coordination and supramolecular recognition properties is of considerable interest for crystal engineering. Herein, we report the synthesis of four new diaminotriazinyl-functionalized oligopyridine mimics, Py2DAT, PyDAT2, m-qtpy, and m-qpy, obtained in excellent yields (>90%) through a simple and efficient synthetic strategy. These compounds were conceived as structural analogues of classical oligopyridines in which selected pyridine units are replaced by diaminotriazinyl (DAT) groups, introducing complementary hydrogen-bond donor and acceptor sites. Comprehensive characterization by NMR, Fourier transform infrared spectroscopy (FTIR), HRMS, ultraviolet–visible (UV–vis) spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction confirmed the structures and revealed remarkable supramolecular organization in the solid state. The DAT groups act as robust supramolecular synthons, directing self-assembly through predictable N–H···N hydrogen-bonding interactions involving both DAT and pyridyl nitrogen atoms. Depending on the molecular topology, the compounds generate crystal architectures ranging from discrete dimers to two-dimensional networks, bilayer assemblies, and ribbon-like structures. The progressive incorporation of DAT units enables precise modulation of molecular geometry, hydrogen-bonding motifs, and crystal packing. These DAT-functionalized oligopyridine mimics constitute a new family of multifunctional building blocks combining hydrogen-bonding motifs with oligopyridine-like coordination sites, making them promising candidates for future coordination-driven supramolecular architectures. Preliminary docking studies further indicate favorable molecular recognition toward DNA and enzyme targets, highlighting the multifunctional character of these bioinspired building blocks.
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DOI: 10.1021/acs.cgd.6c00910
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