Application of a tetrapyrimidyl cyclobutane synthesized in the organic solid state: a halogen-bonded supramolecular ladder

A halogen-bonded supramolecular ladder comprised of a novel pyrimidine-based cyclobutane photoproduct synthesized in the organic solid state via a [2 + 2] photoreaction is reported. The photoproduct rctt-tetrakis(5′-pyrimidyl)cyclobutane functions as rungs while the linear divergent halogen-bond donor 1,4-diiodoperchlorobenzene acts as the rails. Our report also confirms the structure and stereochemistry of the tetrapyrimidyl cyclobutane ring system.

[1]  E. Elacqua,et al.  A diamondoid net sustained by halogen bonds: employing a cyclobutane to generate a tetrahedral architecture , 2020 .

[2]  E. Bosch,et al.  Ditopic halogen bonding with bipyrimidines and activated pyrimidines. , 2020, Acta crystallographica. Section C, Structural chemistry.

[3]  Leonard R. MacGillivray,et al.  Supramolecular Sandwiches: Halogen-Bonded Coformers Direct [2+2] Photoreactivity in Two-Component Cocrystals , 2020, Molecules.

[4]  Gregory S. Tschumper,et al.  A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors , 2019, Inorganics.

[5]  D. Proserpio,et al.  Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds , 2019, IUCrJ.

[6]  Takayoshi Nakamura,et al.  Designing Hydrogen-Bonded Organic Frameworks (HOFs) with Permanent Porosity. , 2019, Angewandte Chemie.

[7]  Michael A. Sinnwell,et al.  Structural flexibility of halogen bonds showed in a single-crystal-to-single-crystal [2+2] photodimerization , 2018, IUCrJ.

[8]  Ying‐Feng Han,et al.  Template-Directed Photochemical [2 + 2] Cycloaddition in Crystalline Materials: A Useful Tool to Access Cyclobutane Derivatives , 2017 .

[9]  Gregory S. Tschumper,et al.  Quantifying the Effects of Halogen Bonding by Haloaromatic Donors on the Acceptor Pyrimidine. , 2017, Chemphyschem : a European journal of chemical physics and physical chemistry.

[10]  M. Ward,et al.  Versatile and Resilient Hydrogen-Bonded Host Frameworks. , 2016, Accounts of chemical research.

[11]  V. Ramamurthy,et al.  Supramolecular Photochemistry as a Potential Synthetic Tool: Photocycloaddition. , 2016, Chemical reviews.

[12]  B. K. Saha,et al.  A product of a templated solid-state photodimerization acts as a template: single-crystal reactivity in a single polymorph of a cocrystal. , 2013, Organic letters.

[13]  K. Biradha,et al.  Crystal engineering of topochemical solid state reactions. , 2013, Chemical Society reviews.

[14]  P. Metrangolo,et al.  Halogen-bonded and interpenetrated networks through the self-assembly of diiodoperfluoroarene and tetrapyridyl tectons , 2010 .

[15]  E. Bosch,et al.  Solid‐State Photodimerization of 1,2‐Bis(5′‐pyrimidyl)ethene , 2007 .

[16]  A. Sokolov,et al.  Supramolecular Ladders: Self-Assembly Fintium to Adfintium , 2006 .

[17]  K. A. Padmanabhan,et al.  Isostructurality, polymorphism and mechanical properties of some hexahalogenated benzenes: the nature of halogen...halogen interactions. , 2006, Chemistry.

[18]  P. Metrangolo,et al.  Halogen bonding and pi...pi stacking control reactivity in the solid state. , 2004, Journal of the American Chemical Society.