Mechanical Force-Induced Blue-Shifted and Enhanced Emission for AIEgens

Mechanochromic (MC) luminescence of organic molecules has been emerging as a promising smart material for optical recording and memory devices. At the same time, pressure-induced blue-shifted and enhanced luminescence are rarely reported now. Herein, a series of cyanostilbene-based AIEgens with different substituents were synthesized to evaluate the influence of morphology transformation and push-pull electronic effect on the MC luminescence. Among these luminophores, compound 1 with one cyano group and diethylamino group was more susceptible to mechanical stimuli and obtained blue-shifted and enhanced fluorescence in response to anisotropic grinding. Powder X-ray diffraction patterns indicated that the MC behaviors were ascribed to the solid-state morphology transition from crystal-to-crystal. Analysis of crystal structures revealed that loose molecular packing is a key factor for high high-contrast MC luminescence. The smart molecular design, together with the excellent performance, verified that luminophores with twisted structures are ideal candidates for MC luminogens.

[1]  Chunxuan Qi,et al.  Visualization of Enantiorecognition and Resolution by Chiral AIEgens. , 2022, ACS nano.

[2]  P. Stang,et al.  Metallacycles, metallacages, and their aggregate/optical behavior , 2021, Aggregate.

[3]  B. Tang,et al.  Organometallic AIEgens for biological theranostics , 2021 .

[4]  B. Tang,et al.  A synergy between the push-pull electronic effect and twisted conformation for high-contrast mechanochromic AIEgens. , 2020, Materials horizons.

[5]  Zhen Li,et al.  Organic luminescent materials: The concentration on aggregates from aggregation‐induced emission , 2020, Aggregate.

[6]  D. Ding,et al.  Substitution Activated Precise Phototheranostics through Supramolecular Assembly of AIEgen and Calixarene. , 2020, Journal of the American Chemical Society.

[7]  Ian D. Williams,et al.  Molecular Motions in AIEgen Crystals: Turning on Photoluminescence by Force-Induced Filament Sliding. , 2020, Journal of the American Chemical Society.

[8]  B. Tang,et al.  Aggregation-induced emission luminogen for specific identification of malignant tumour in vivo , 2020, Science China Chemistry.

[9]  Gang Chen,et al.  Pressure-Induced Blue-Shifted and Enhanced Emission: A Cooper-ative Effect between Aggregation-Induced Emission and Energy-Transfer Suppression. , 2020, Journal of the American Chemical Society.

[10]  M. Yao,et al.  Pressure-Induced Emission Enhancement and Multi-color for 1, 2, 3, 4-tetraphenyl-1, 3-cyclopentadiene (TPC)：Controlled Structure Evolution. , 2019, The journal of physical chemistry letters.

[11]  D. Shen,et al.  Surface related intrinsic luminescence from carbon nanodots: solvent dependent piezochromism. , 2019, Nanoscale horizons.

[12]  M. Yao,et al.  Pressure-Induced Emission Enhancement and Multicolor Emission for 1,2,3,4-Tetraphenyl-1,3-cyclopentadiene: Controlled Structure Evolution , 2019 .

[13]  Bo Zou,et al.  Piezochromic Luminescence of Donor-Acceptor Cocrystals: Distinct Responses to Anisotropic Grinding and Isotropic Compression. , 2018, Angewandte Chemie.

[14]  B. Tang,et al.  Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect. , 2018, Chemical Society reviews.

[15]  M. P. Aldred,et al.  Recent advances in mechano-responsive luminescence of tetraphenylethylene derivatives with aggregation-induced emission properties , 2018 .

[16]  D. Pang,et al.  Mechanofluorochromic Carbon Nanodots: Controllable Pressure-Triggered Blue- and Red-Shifted Photoluminescence. , 2018, Angewandte Chemie.

[17]  Zhen Li,et al.  Molecular conformation and packing: their critical roles in the emission performance of mechanochromic fluorescence materials , 2017 .

[18]  Bo Zou,et al.  Pressure-Induced Emission Enhancement of Carbazole: The Restriction of Intramolecular Vibration. , 2017, The journal of physical chemistry letters.

[19]  Bai Yang,et al.  Piezochromic Carbon Dots with Two-photon Fluorescence. , 2017, Angewandte Chemie.

[20]  Yuguang Ma,et al.  Rehybridization of Nitrogen Atom Induced Photoluminescence Enhancement under Pressure Stimulation , 2017 .

[21]  Zhen Li,et al.  A stable tetraphenylethene derivative: aggregation-induced emission, different crystalline polymorphs, and totally different mechanoluminescence properties , 2016 .

[22]  Christoph Weder,et al.  Mechanoresponsive Luminescent Molecular Assemblies: An Emerging Class of Materials , 2016, Advanced materials.

[23]  Zhimin Ma,et al.  A Mechanochromic Single Crystal: Turning Two Color Changes into a Tricolored Switch. , 2016, Angewandte Chemie.

[24]  Yen Wei,et al.  A Novel Mechanochromic and Photochromic Polymer Film: When Rhodamine Joins Polyurethane , 2015, Advanced materials.

[25]  Ryan T. K. Kwok,et al.  Aggregation-Induced Emission: Together We Shine, United We Soar! , 2015, Chemical reviews.

[26]  Zejun Xu,et al.  Mechanically Induced Multicolor Change of Luminescent Materials. , 2015, Chemphyschem : a European journal of chemical physics and physical chemistry.

[27]  Bo Zou,et al.  Luminescent Chromism of Boron Diketonate Crystals: Distinct Responses to Different Stresses , 2015, Advanced materials.

[28]  Bingbing Liu,et al.  Luminescence Properties of Compressed Tetraphenylethene: The Role of Intermolecular Interactions. , 2014, The journal of physical chemistry letters.

[29]  Hiroyasu Sato,et al.  Distinct responses to mechanical grinding and hydrostatic pressure in luminescent chromism of tetrathiazolylthiophene. , 2013, Journal of the American Chemical Society.

[30]  N. Kitamura,et al.  Mechanical stimulation and solid seeding trigger single-crystal-to-single-crystal molecular domino transformations , 2013, Nature Communications.

[31]  G. Ruggeri,et al.  Dye-containing polymers: methods for preparation of mechanochromic materials. , 2013, Chemical Society reviews.

[32]  张艺,et al.  Recent advances in mechanochromic luminescent metal complexes , 2013 .

[33]  Lijuan Wang,et al.  Piezochromic luminescence based on the molecular aggregation of 9,10-bis((E)-2-(pyrid-2-yl)vinyl)anthracene. , 2012, Angewandte Chemie.

[34]  Jia-rui Xu,et al.  Recent advances in organic mechanofluorochromic materials. , 2012, Chemical Society reviews.

[35]  Y. Ooyama,et al.  Molecular design of mechanofluorochromic dyes and their solid-state fluorescence properties , 2011 .

[36]  Dongho Kim,et al.  Multistimuli two-color luminescence switching via different slip-stacking of highly fluorescent molecular sheets. , 2010, Journal of the American Chemical Society.

[37]  Takashi Kato,et al.  Mechanically induced luminescence changes in molecular assemblies. , 2009, Nature chemistry.

[38]  C. Weder,et al.  Oligo(p-phenylene vinylene) Excimers as Molecular Probes: Deformation-Induced Color Changes in Photoluminescent Polymer Blends , 2002 .

[39]  B. Hsieh,et al.  Aggregation Quenching of Luminescence in Electroluminescent Conjugated Polymers , 1999 .

[40]  Uli Lemmer,et al.  AGGREGATE FLUORESCENCE IN CONJUGATED POLYMERS , 1995 .