{"title":"Engineering Isomeric AIEgens Containing Tetraphenylpyrazine for Dual Memory Storage","authors":"Zicheng Liu, Wenhao Wang, Hongfei Liao, Runfeng Lin, Xiang He, Canze Zheng, Changsheng Guo, Hongguang Liu*, Hai-Tao Feng and Ming Chen*, ","doi":"10.1021/cbmi.3c00048","DOIUrl":null,"url":null,"abstract":"<p >Tetraphenylpyrazine (TPP) is a promising heterocycle-based aggregation-induced emission luminogen (AIEgen) which has sparked multiple applications in organic light-emitting diodes, sensors, and biotherapy. However, the utility of it in developing information storage materials is relatively rare. Moreover, TPP is mostly employed as an electronic acceptor in molecular design, while the consideration of it as an electronic donor is attractive in studies which may provide a full understanding of its property to tailor the materials. In this work, we synthesize three TPP-based molecules by decorating it with acrylonitrile and isomeric pyridine units, which show AIE behavior by property inheritance from their parent unit. Interestingly, the effective intramolecular charge transfer takes place from the TPP electronic donor to the acrylonitrile and pyridine electronic acceptor, therefore inducing a remarkable solvatochromic effect as the solvent polarity improves. Moreover, it is revealed that the isomeric effect of the nitrogen atom in the pyridines may pose an influence on the absorption, solvatochromism, and AIE behavior. In addition, the acrylonitrile and pyridine groups are reactive to light and acid–base stimuli with irreversible and reversible responses, respectively. Combined with the high light-harvesting ability of these AIEgens, they show great potential in the stimuli-responsive materials for dual information storage.</p>","PeriodicalId":53181,"journal":{"name":"Chemical & Biomedical Imaging","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/cbmi.3c00048","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical & Biomedical Imaging","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/cbmi.3c00048","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Tetraphenylpyrazine (TPP) is a promising heterocycle-based aggregation-induced emission luminogen (AIEgen) which has sparked multiple applications in organic light-emitting diodes, sensors, and biotherapy. However, the utility of it in developing information storage materials is relatively rare. Moreover, TPP is mostly employed as an electronic acceptor in molecular design, while the consideration of it as an electronic donor is attractive in studies which may provide a full understanding of its property to tailor the materials. In this work, we synthesize three TPP-based molecules by decorating it with acrylonitrile and isomeric pyridine units, which show AIE behavior by property inheritance from their parent unit. Interestingly, the effective intramolecular charge transfer takes place from the TPP electronic donor to the acrylonitrile and pyridine electronic acceptor, therefore inducing a remarkable solvatochromic effect as the solvent polarity improves. Moreover, it is revealed that the isomeric effect of the nitrogen atom in the pyridines may pose an influence on the absorption, solvatochromism, and AIE behavior. In addition, the acrylonitrile and pyridine groups are reactive to light and acid–base stimuli with irreversible and reversible responses, respectively. Combined with the high light-harvesting ability of these AIEgens, they show great potential in the stimuli-responsive materials for dual information storage.
期刊介绍:
Chemical & Biomedical Imaging is a peer-reviewed open access journal devoted to the publication of cutting-edge research papers on all aspects of chemical and biomedical imaging. This interdisciplinary field sits at the intersection of chemistry physics biology materials engineering and medicine. The journal aims to bring together researchers from across these disciplines to address cutting-edge challenges of fundamental research and applications.Topics of particular interest include but are not limited to:Imaging of processes and reactionsImaging of nanoscale microscale and mesoscale materialsImaging of biological interactions and interfacesSingle-molecule and cellular imagingWhole-organ and whole-body imagingMolecular imaging probes and contrast agentsBioluminescence chemiluminescence and electrochemiluminescence imagingNanophotonics and imagingChemical tools for new imaging modalitiesChemical and imaging techniques in diagnosis and therapyImaging-guided drug deliveryAI and machine learning assisted imaging