Time-dependent solid-state molecular motion and colour tuning of host-guest systems by organic solvents

Host-guest complex solid state molecular motion is a critical but underexplored phenomenon. In principle, it can be used to control molecular machines that function in the solid state. Here we describe a solid state system that operates on the basis of complexation between an all-hydrocarbon macrocycle, D4d-CDMB-8, and perylene. Molecular motion in this solid state machine is induced by exposure to organic solvents or grinding and gives rise to different co-crystalline, mixed crystalline, or amorphous forms. Distinct time-dependent emissive responses are seen for different organic solvents as their respective vapours or when the solid forms are subject to grinding. This temporal feature allows the present D4d-CDMB-8⊃perylene-based system to be used as a time-dependent, colour-based 4th dimension response element in pattern-based information codes. This work highlights how dynamic control over solid-state host-guest molecular motion may be used to induce a tuneable temporal response and provide materials with information storage capability.Host-guest solid state molecular motion is a critical but underexplored phenomenon which can be used to control molecular machines that function in the solid state. Here, the authors describe a solid state machine that shows solvent vapour- and mechanically-induced molecular motion that allows access to different crystalline and amorphous forms.

[1]  Ryan T. K. Kwok,et al.  Highly efficient photothermal nanoagent achieved by harvesting energy via excited-state intramolecular motion within nanoparticles , 2019, Nature Communications.

[2]  Linbing Sun,et al.  Metal-Organic Frameworks for Heterogeneous Basic Catalysis. , 2017, Chemical reviews.

[3]  M. Garcia‐Garibay,et al.  Crystalline molecular machines: function, phase order, dimensionality, and composition. , 2012, Chemical Society reviews.

[4]  Jean-Pierre Sauvage,et al.  Molecular Catenanes, Rotaxanes and Knots , 1999 .

[5]  Daniel J. Tetlow,et al.  Rotary and linear molecular motors driven by pulses of a chemical fuel , 2017, Science.

[6]  K. Lava,et al.  Ionic Liquid Crystals: Versatile Materials. , 2016, Chemical reviews.

[7]  Kristopher J Harris,et al.  Metal-organic frameworks with dynamic interlocked components. , 2012, Nature chemistry.

[8]  Reiner Sebastian Sprick,et al.  Sulfone-containing covalent organic frameworks for photocatalytic hydrogen evolution from water , 2018, Nature Chemistry.

[9]  Jing Li,et al.  Metal-organic frameworks: functional luminescent and photonic materials for sensing applications. , 2017, Chemical Society reviews.

[10]  Kecheng Jie,et al.  Supramolecular Amphiphiles Based on Host-Guest Molecular Recognition Motifs. , 2015, Chemical reviews.

[11]  Quan Li,et al.  Photochromism into nanosystems: towards lighting up the future nanoworld. , 2018, Chemical Society reviews.

[12]  M. Garcia‐Garibay,et al.  Rotation of a bulky triptycene in the solid state: toward engineered nanoscale artificial molecular machines. , 2014, Journal of the American Chemical Society.

[13]  M. Titirici,et al.  Nanoporous Materials for the Onboard Storage of Natural Gas. , 2017, Chemical reviews.

[14]  James A. Ibers,et al.  International tables for X-ray crystallography , 1962 .

[15]  M. Beller,et al.  Reduction of Nitro Compounds Using 3d-Non-Noble Metal Catalysts. , 2018, Chemical reviews.

[16]  J. F. Stoddart,et al.  Robust dynamics. , 2010, Nature chemistry.

[17]  Molecular Diffusion–Driven Motion in 2D Graphene Film , 2018 .

[18]  Kelong Zhu,et al.  A molecular shuttle that operates inside a metal-organic framework. , 2015, Nature chemistry.

[19]  J. C. Barnes,et al.  Induced-fit catalysis of corannulene bowl-to-bowl inversion. , 2014, Nature chemistry.

[20]  Ki‐Hyun Kim,et al.  Functional hybrid nanostructure materials: Advanced strategies for sensing applications toward volatile organic compounds , 2017 .

[21]  Li-Ya Niu,et al.  A Solid‐State Fluorescent Material Based on Carbazole‐Containing Difluoroboron β‐Diketonate: Multiple Chromisms, the Self‐Assembly Behavior, and Optical Waveguides , 2017 .

[22]  Ian D. Williams,et al.  Spontaneous and Fast Molecular Motion at Room Temperature in the Solid State. , 2019, Angewandte Chemie.

[23]  E. W. Meijer,et al.  Making waves in a photoactive polymer film , 2017, Nature.

[24]  C. Weder,et al.  Bio‐Inspired, Self‐Toughening Polymers Enabled by Plasticizer‐Releasing Microcapsules , 2019, Advanced materials.

[25]  Yuguang Ma,et al.  CO2 Capture and Separations Using MOFs: Computational and Experimental Studies. , 2017, Chemical reviews.

[26]  Xi-Yan Dong,et al.  Hypersensitive dual-function luminescence switching of a silver-chalcogenolate cluster-based metal-organic framework. , 2017, Nature chemistry.

[27]  G. Sheldrick SHELXT – Integrated space-group and crystal-structure determination , 2015, Acta crystallographica. Section A, Foundations and advances.

[28]  M. Zelsmann,et al.  Ultrafast Assembly of PS‐PDMS Block Copolymers on 300 mm Wafers by Blending with Plasticizers , 2016 .

[29]  O. Yaghi,et al.  The role of reticular chemistry in the design of CO2 reduction catalysts , 2018, Nature Materials.

[30]  H. Gong,et al.  Thermally activated isomeric all-hydrocarbon molecular receptors for fullerene separation. , 2019, Chemical communications.

[31]  O. Yaghi,et al.  Carbon capture and conversion using metal-organic frameworks and MOF-based materials. , 2019, Chemical Society reviews.

[32]  Elena Boldyreva,et al.  Mechanically Responsive Molecular Crystals. , 2015, Chemical reviews.

[33]  Huanli Dong,et al.  Solvatomechanical Bending of Organic Charge Transfer Cocrystal. , 2018, Journal of the American Chemical Society.

[34]  H. Isobe,et al.  Retarded solid-state rotations of an oval-shaped guest in a deformed cylinder with CH-π arrays. , 2019, Angewandte Chemie.

[35]  Kristopher J Harris,et al.  Mechanically Interlocked Linkers inside Metal-Organic Frameworks: Effect of Ring Size on Rotational Dynamics. , 2015, Journal of the American Chemical Society.

[36]  Omar M. Yaghi,et al.  The role of metal–organic frameworks in a carbon-neutral energy cycle , 2016, Nature Energy.

[37]  Hiroyasu Sato,et al.  Mechanical-Stimulation-Triggered and Solvent-Vapor-Induced Reverse Single-Crystal-to-Single-Crystal Phase Transitions with Alterations of the Luminescence Color. , 2018, Journal of the American Chemical Society.

[38]  K. M. Sureshan,et al.  Spontaneous Single-Crystal-to-Single-Crystal Evolution of Two Cross-Laminated Polymers. , 2018, Angewandte Chemie.

[39]  Bin Liu,et al.  Visualizing the Initial Step of Self-Assembly and the Phase Transition by Stereogenic Amphiphiles with Aggregation-Induced Emission. , 2018, ACS nano.

[40]  Kuan-Yi Wu,et al.  Polymorphic Behavior of Perylene and Its Influences on OFET Performances , 2018, The Journal of Physical Chemistry C.

[41]  Vivian Wing-Wah Yam,et al.  Supramolecular Self-Assembly and Dual-Switch Vapochromic, Vapoluminescent, and Resistive Memory Behaviors of Amphiphilic Platinum(II) Complexes. , 2017, Journal of the American Chemical Society.

[42]  C. Tschierske Development of structural complexity by liquid-crystal self-assembly. , 2013, Angewandte Chemie.

[43]  Nathalie Katsonis,et al.  Shape-Persistent Actuators from Hydrazone Photoswitches , 2019, Journal of the American Chemical Society.

[44]  Xiang Ma,et al.  Photoresponsive Host-Guest Functional Systems. , 2015, Chemical reviews.

[45]  R. Lu,et al.  Bending, Curling, Rolling, and Salient Behavior of Molecular Crystals Driven by [2+2] Cycloaddition of a Styrylbenzoxazole Derivative. , 2017, Angewandte Chemie.

[46]  Y. Maniwa,et al.  Ratchet-free solid-state inertial rotation of a guest ball in a tight tubular host , 2018, Nature Communications.