[(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State
Developing a new type of circularly polarized luminescent active small organic molecule that combines high fluorescence quantum yield and luminescence dissymmetric factor in both solution and solid state is highly challenging but promising. In this context, we designed and synthesized a unique triar...
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2025-01-01
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| author | Lianfeng Guo Mengyuan Zhang Cuihua Zhao |
| author_facet | Lianfeng Guo Mengyuan Zhang Cuihua Zhao |
| author_sort | Lianfeng Guo |
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| description | Developing a new type of circularly polarized luminescent active small organic molecule that combines high fluorescence quantum yield and luminescence dissymmetric factor in both solution and solid state is highly challenging but promising. In this context, we designed and synthesized a unique triarylborane-based [2.2]paracyclophane derivative, <b><i>m</i>-BPhANPh<sub>2</sub>-Cp</b>, in which an electron-accepting [(2-dimesitylboryl)phenyl]ethynyl group and an electron-donating <i>N,N</i>-diphenylamino group are introduced into two different benzene rings of [2.2]paracyclophane. Owing to the electronic effect of these two substituents, this compound can display charge-transfer emission with large Stokes shifts (∆<i>υ</i> = 4.23 − 8.20 × 10<sup>3</sup> cm<sup>−1</sup>) and fair quantum yields (<i>Φ</i><sub>F</sub> = 0.15 − 0.37) in solutions. In addition, this compound can emit strong blue fluorescence in the solid state with quantum yields that are even much higher than in solution (<i>Φ</i><sub>F</sub> up to 0.64 in powder and spin-coated film). Moreover, the enantiomeric forms of <b><i>m</i>-BPhANPh<sub>2</sub>-Cp</b> can show strong CPL signals in both dilute solution and solid state with |<i>g</i><sub>lum</sub>|s up to 9.6 × 10<sup>−3</sup> and 5.4 × 10<sup>−3</sup>, respectively. Thus, it is possible to achieve tunable CPL from blue to yellow in solution with high <i>B</i><sub>CPL</sub>s ranging from 56.7 to 26.6 M<sup>−1</sup> cm<sup>−1</sup> and intense blue CPL combing high <i>Φ</i><sub>F</sub> and |<i>g</i><sub>lum</sub>| in the solid state. |
| format | Article |
| id | doaj-art-95d3b7a0a4ca4d05af6d9fa99330e09e |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
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| spelling | doaj-art-95d3b7a0a4ca4d05af6d9fa99330e09e2025-01-24T13:43:53ZengMDPI AGMolecules1420-30492025-01-0130239010.3390/molecules30020390[(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-StateLianfeng Guo0Mengyuan Zhang1Cuihua Zhao2School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, ChinaCollege of Chemical Engineering and Environmental Engineering, Weifang University, Weifang 261061, ChinaSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, ChinaDeveloping a new type of circularly polarized luminescent active small organic molecule that combines high fluorescence quantum yield and luminescence dissymmetric factor in both solution and solid state is highly challenging but promising. In this context, we designed and synthesized a unique triarylborane-based [2.2]paracyclophane derivative, <b><i>m</i>-BPhANPh<sub>2</sub>-Cp</b>, in which an electron-accepting [(2-dimesitylboryl)phenyl]ethynyl group and an electron-donating <i>N,N</i>-diphenylamino group are introduced into two different benzene rings of [2.2]paracyclophane. Owing to the electronic effect of these two substituents, this compound can display charge-transfer emission with large Stokes shifts (∆<i>υ</i> = 4.23 − 8.20 × 10<sup>3</sup> cm<sup>−1</sup>) and fair quantum yields (<i>Φ</i><sub>F</sub> = 0.15 − 0.37) in solutions. In addition, this compound can emit strong blue fluorescence in the solid state with quantum yields that are even much higher than in solution (<i>Φ</i><sub>F</sub> up to 0.64 in powder and spin-coated film). Moreover, the enantiomeric forms of <b><i>m</i>-BPhANPh<sub>2</sub>-Cp</b> can show strong CPL signals in both dilute solution and solid state with |<i>g</i><sub>lum</sub>|s up to 9.6 × 10<sup>−3</sup> and 5.4 × 10<sup>−3</sup>, respectively. Thus, it is possible to achieve tunable CPL from blue to yellow in solution with high <i>B</i><sub>CPL</sub>s ranging from 56.7 to 26.6 M<sup>−1</sup> cm<sup>−1</sup> and intense blue CPL combing high <i>Φ</i><sub>F</sub> and |<i>g</i><sub>lum</sub>| in the solid state.https://www.mdpi.com/1420-3049/30/2/390[2.2]paracyclophanetriarylboranecircularly polarized luminescencehigh emission efficiencyhigh luminescence dissymmetry factor |
| spellingShingle | Lianfeng Guo Mengyuan Zhang Cuihua Zhao [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State Molecules [2.2]paracyclophane triarylborane circularly polarized luminescence high emission efficiency high luminescence dissymmetry factor |
| title | [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State |
| title_full | [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State |
| title_fullStr | [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State |
| title_full_unstemmed | [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State |
| title_short | [(2-Dimesitylboryl)phenyl]ethynyl-Substituted [2.2]Paracyclophane Exhibiting Circularly Polarized Luminescence in Both Solution and Solid-State |
| title_sort | 2 dimesitylboryl phenyl ethynyl substituted 2 2 paracyclophane exhibiting circularly polarized luminescence in both solution and solid state |
| topic | [2.2]paracyclophane triarylborane circularly polarized luminescence high emission efficiency high luminescence dissymmetry factor |
| url | https://www.mdpi.com/1420-3049/30/2/390 |
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