Unconventional, Gram-Scale Synthesis of a Molecular Dimer Organic Luminogen with Aggregation-Induced Emission
Organic luminogens have been widely used in optoelectronic devices, bioimaging, and sensing. Conventionally, the synthesis of organic luminogens requires sophisticated, multistep design, reaction, and isolation procedures. Herein, the products of the melt-phase condensation of benzoguanamine (BG; 2,...
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Published in | ACS applied materials & interfaces Vol. 13; no. 34; pp. 40441 - 40450 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
01.09.2021
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Abstract | Organic luminogens have been widely used in optoelectronic devices, bioimaging, and sensing. Conventionally, the synthesis of organic luminogens requires sophisticated, multistep design, reaction, and isolation procedures. Herein, the products of the melt-phase condensation of benzoguanamine (BG; 2,4-diamino-6-phenyl-1,3,5-triazine) at 370–410 °C display interesting reaction-condition-dependent luminescence properties, including photoluminescence (PL) at a variety of wavelengths in the visible spectrum and quantum efficiencies (PLQE) of up to 58% in the powder form. With a simple and straightforward solvent washing procedure, the prominent blue luminescent component BG dimer was obtained in gram scale with >93% purity (96.5% purity after fractional sublimation). The BG dimer exhibited distinct aggregation-induced emission (AIE) properties. PL measurements indicate that the electronically excited state of the BG dimer undergoes efficient intramolecular nonradiative deactivation in room-temperature solution, leading to a significantly reduced PLQE (<0.1%) in solution. These nonradiative processes are substantially inhibited when the dimer existed in the form of crystals, solid aggregates in solution or being fixed in a rigid polymer film, resulting in a significant increase in the PLQE and lifetime. This work not only provided a new understanding for PL properties of self-condensation luminescent products but also represented an unconventional strategy for large-scale preparation of organic luminogens with high purity. |
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AbstractList | Organic luminogens have been widely used in optoelectronic devices, bioimaging, and sensing. Conventionally, the synthesis of organic luminogens requires sophisticated, multistep design, reaction, and isolation procedures. Herein, the products of the melt-phase condensation of benzoguanamine (BG; 2,4-diamino-6-phenyl-1,3,5-triazine) at 370–410 °C display interesting reaction-condition-dependent luminescence properties, including photoluminescence (PL) at a variety of wavelengths in the visible spectrum and quantum efficiencies (PLQE) of up to 58% in the powder form. With a simple and straightforward solvent washing procedure, the prominent blue luminescent component BG dimer was obtained in gram scale with >93% purity (96.5% purity after fractional sublimation). The BG dimer exhibited distinct aggregation-induced emission (AIE) properties. PL measurements indicate that the electronically excited state of the BG dimer undergoes efficient intramolecular nonradiative deactivation in room-temperature solution, leading to a significantly reduced PLQE (<0.1%) in solution. These nonradiative processes are substantially inhibited when the dimer existed in the form of crystals, solid aggregates in solution or being fixed in a rigid polymer film, resulting in a significant increase in the PLQE and lifetime. This work not only provided a new understanding for PL properties of self-condensation luminescent products but also represented an unconventional strategy for large-scale preparation of organic luminogens with high purity. |
Author | Hirai, Tadahiko Brock, Aidan J Skidmore, Melissa Han, Chenhui Xiao, Qi Xu, Jingsan McMurtrie, John C Meng, Peng Scully, Andrew D Chesman, Anthony S. R |
AuthorAffiliation | State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering School of Chemistry and Physics & Centre for Materials Science Ian Wark Laboratories |
AuthorAffiliation_xml | – name: School of Chemistry and Physics & Centre for Materials Science – name: Ian Wark Laboratories – name: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering |
Author_xml | – sequence: 1 givenname: Peng orcidid: 0000-0002-4624-2430 surname: Meng fullname: Meng, Peng organization: School of Chemistry and Physics & Centre for Materials Science – sequence: 2 givenname: Chenhui surname: Han fullname: Han, Chenhui organization: School of Chemistry and Physics & Centre for Materials Science – sequence: 3 givenname: Andrew D orcidid: 0000-0003-3116-3067 surname: Scully fullname: Scully, Andrew D organization: Ian Wark Laboratories – sequence: 4 givenname: Qi orcidid: 0000-0001-6691-3986 surname: Xiao fullname: Xiao, Qi email: qi.xiao@dhu.edu.cn organization: State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering – sequence: 5 givenname: Aidan J surname: Brock fullname: Brock, Aidan J organization: School of Chemistry and Physics & Centre for Materials Science – sequence: 6 givenname: Tadahiko surname: Hirai fullname: Hirai, Tadahiko organization: Ian Wark Laboratories – sequence: 7 givenname: Melissa surname: Skidmore fullname: Skidmore, Melissa organization: Ian Wark Laboratories – sequence: 8 givenname: John C orcidid: 0000-0003-3990-8617 surname: McMurtrie fullname: McMurtrie, John C organization: School of Chemistry and Physics & Centre for Materials Science – sequence: 9 givenname: Anthony S. R orcidid: 0000-0002-1807-4468 surname: Chesman fullname: Chesman, Anthony S. R organization: Ian Wark Laboratories – sequence: 10 givenname: Jingsan orcidid: 0000-0003-1172-3864 surname: Xu fullname: Xu, Jingsan email: jingsan.xu@qut.edu.au organization: School of Chemistry and Physics & Centre for Materials Science |
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Title | Unconventional, Gram-Scale Synthesis of a Molecular Dimer Organic Luminogen with Aggregation-Induced Emission |
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