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. 2022 Nov 2;9(11):220603.
doi: 10.1098/rsos.220603. eCollection 2022 Nov.

Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds

Shazia Asghar  1 , Shahid Hameed  1 , Muhammad Nawaz Tahir  2 , Muhammad Moazzam Naseer  1
Affiliations

Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds

Shazia Asghar et al. R Soc Open Sci. .

Abstract

Synthetic supramolecular structures constructed through the cooperative action of numerous non-covalent forces are highly desirable as models to unravel and understand the complexity of systems created in nature via self-assembly. Taking advantage of the low cost of 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) and the sequential nucleophilic substitution reactions with almost all types of nucleophiles, a series of six structurally related novel s-triazine derivatives 1-6 were synthesized and structurally characterized based on their physical, spectral and crystallographic data. The solid-state structures of all the six compounds showed intriguing and unique molecular duplexes featuring NH···N, CH···O and CH···π interactions. Careful analysis of different geometric parameters of the involved H-bonds indicates that they are linear, significant and are therefore responsible for guiding the three-dimensional structure of these compounds in the solid state. The prevalence of sextuple hydrogen bond array-driven molecular duplexes and the possibility of structural modifications on the s-triazine ring render these novel triazine derivatives 1-6 attractive as a platform to create heteroduplex constructs and their subsequent utility in the field of supramolecular chemistry and crystal engineering.

Keywords: CH···O interactions; CH···π interactions; molecular duplexes; self-assembly; supramolecular synthons; triazine derivatives.

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Conflict of interest statement

We declare we have no competing interests.

Figures

Figure 1.
Figure 1.
Proposed general structural features of synthesized triazine derivatives. Note: in cases where n = 0, neighbouring aryl CH may act as weak H-bond donor.
Scheme 1.
Scheme 1.
Synthesis of s-triazine derivatives 1–6.
Figure 2.
Figure 2.
The molecular structures (Oak Ridge thermal ellipsoid plot (ORTEP) diagram) of triazine derivatives 1–6. Displacement ellipsoids are drawn at 50% probability level.
Figure 3.
Figure 3.
Molecular duplexes observed in the solid-state structures of triazine derivatives 1–6.
See this image and copyright information in PMC

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