Chinese Journal of Organic Chemistry >
Synthesis of Donor-Acceptor (D-A) Typed Phenylcyclooctatetrathiophenes and Their Performances on Aggregation Induced Emission and High Pressure Luminescence
Received date: 2024-04-01
Revised date: 2024-06-21
Online published: 2024-07-10
Supported by
National Natural Science Foundation of China(U2004213); National Natural Science Foundation of China(21672053); Organic Functional Materials Technology Innovation Team of Henan Province(C20150011)
The saddle-shaped cyclooctatetrathiophene (COTh) is an interesting aggregation induced emission (AIE) molecule. In this work, the strong electron withdrawing group (CN) and the strong electron donating group (OMe) are introduced into the ortho, meta and para positions of benzene ring, reacting with COTh unit through Suzuki reaction to construct six donor-acceptor (D-A) typed substituted phenyl Ar-COTh compounds. The single crystal structure of p-OMe-Ph-COTh shows multiple intermolecular interactions, such as S…C, C…O and O…H interactions among molecules. These D-A typed Ar-COThs exhibit significant AIE luminescence properties, which are mainly attributed to the intramolecular through space conjugation (ITSC) of COTh in excited state. The weak correlation between the emission peak and the substituent effect is observed. The fluorescence quantum yields of Ar-COThs in solid-state luminescence are higher than that of AIE state. Under high pressure, the emission peak of p-CN-Ph-COTh containing strong electron withdrawing group (CN) showed strong bathochromic shift from 531 nm to 634 nm with a big difference of 103 nm under the external pressure change from 0.00 to 8.86 GPa; However, the emission peak of p-OMe-Ph-COTh containing electron donating group (OMe) gave the only change of 29 nm under the pressure change from 0.00 to 12.0 GPa, demonstrating significant substituent and piezochromic effects.
Yujie Yang , Wei Cao , Jikai Yu , Zhixia Zhang , Li Xu , Hua Wang . Synthesis of Donor-Acceptor (D-A) Typed Phenylcyclooctatetrathiophenes and Their Performances on Aggregation Induced Emission and High Pressure Luminescence[J]. Chinese Journal of Organic Chemistry, 2024 , 44(8) : 2495 -2503 . DOI: 10.6023/cjoc202404001
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