Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy
Abstract Creation of new fluorophores is important for understanding the structure–property relationship, by which the required optical properties are likely to be attained. Herein, through theory calculation, it is found that furan‐modified thiadiazolo quinoxaline acting as an electron acceptor can...
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Wiley
2024-04-01
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| Series: | Aggregate |
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| Online Access: | https://doi.org/10.1002/agt2.458 |
| _version_ | 1797207128143822848 |
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| author | Mengke Liang Luyu Liu Ying Sun Jia Li Ling'e Zhang Xiqun Jiang Wei Wu |
| author_facet | Mengke Liang Luyu Liu Ying Sun Jia Li Ling'e Zhang Xiqun Jiang Wei Wu |
| author_sort | Mengke Liang |
| collection | DOAJ |
| description | Abstract Creation of new fluorophores is important for understanding the structure–property relationship, by which the required optical properties are likely to be attained. Herein, through theory calculation, it is found that furan‐modified thiadiazolo quinoxaline acting as an electron acceptor can endow donor–acceptor–donor (D–A–D) type second near‐infrared (NIR‐II) fluorophores with longer emission wavelength than the other thiadiazolo quinoxaline‐based acceptors containing pyridine, pyrrole, thiophene, and phenyl groups, respectively. On the basis of this theoretical prediction, a D–A–D type NIR‐II fluorophore with 6,7‐di(furan‐2‐yl)‐[1,2,5]thiadiazolo[3,4‐g] quinoxaline (DFTQ) as the acceptor and dithieno[3,2‐b:2′,3′‐d]pyrrole (DTP) as the donor is designed and synthesized, and the aggregation‐induced emission (AIE) function is further achieved by introducing the AIE units of tetraphenylethylene (TPE) and triphenylamine (TPA), respectively, totally forming three NIR‐II fluorophores DFTQ–DTP, DFTQ–DTPE, and DFTQ–DTPA. For biological applications, the fluorophores are encapsulated by amphiphilic DSPE–PEG2000 to generate water‐dispersible nanoparticles (NPs). Almost the whole emission of each of the NPs falls into the NIR‐II spectral range, with part emission beyond 1300 nm. By using DFTQ–DTPA NPs as the contrast and photothermal therapy (PTT) agent, high‐resolution in vivo fluorescence imaging is achieved in the greater than 1300 nm window, and their good performance in photoacoustic imaging and high tumor PTT efficacy in tumor‐bearing mice are also demonstrated. Taken together, this work mainly provides a strong electron acceptor for constructing long‐emitting fluorophores, and by using the electron acceptor, a AIE fluorophore with desirable quantum yield (QY) and photothermal conversion efficienciy (PCE) is synthesized and demonstrated to be promising in fluorescence/photoacoustic imaging and PTT. |
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| institution | Directory Open Access Journal |
| issn | 2692-4560 |
| language | English |
| last_indexed | 2024-04-24T09:17:59Z |
| publishDate | 2024-04-01 |
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| spelling | doaj.art-4a425ba5281743af8d8cedb6a5eb7a742024-04-15T16:27:13ZengWileyAggregate2692-45602024-04-0152n/an/a10.1002/agt2.458Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapyMengke Liang0Luyu Liu1Ying Sun2Jia Li3Ling'e Zhang4Xiqun Jiang5Wei Wu6Department of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaDepartment of Polymer Science & Engineering, State Key Laboratory of Analytical Chemistry for Life Science College of Chemistry & Chemical Engineering, Nanjing University Nanjing P. R. ChinaAbstract Creation of new fluorophores is important for understanding the structure–property relationship, by which the required optical properties are likely to be attained. Herein, through theory calculation, it is found that furan‐modified thiadiazolo quinoxaline acting as an electron acceptor can endow donor–acceptor–donor (D–A–D) type second near‐infrared (NIR‐II) fluorophores with longer emission wavelength than the other thiadiazolo quinoxaline‐based acceptors containing pyridine, pyrrole, thiophene, and phenyl groups, respectively. On the basis of this theoretical prediction, a D–A–D type NIR‐II fluorophore with 6,7‐di(furan‐2‐yl)‐[1,2,5]thiadiazolo[3,4‐g] quinoxaline (DFTQ) as the acceptor and dithieno[3,2‐b:2′,3′‐d]pyrrole (DTP) as the donor is designed and synthesized, and the aggregation‐induced emission (AIE) function is further achieved by introducing the AIE units of tetraphenylethylene (TPE) and triphenylamine (TPA), respectively, totally forming three NIR‐II fluorophores DFTQ–DTP, DFTQ–DTPE, and DFTQ–DTPA. For biological applications, the fluorophores are encapsulated by amphiphilic DSPE–PEG2000 to generate water‐dispersible nanoparticles (NPs). Almost the whole emission of each of the NPs falls into the NIR‐II spectral range, with part emission beyond 1300 nm. By using DFTQ–DTPA NPs as the contrast and photothermal therapy (PTT) agent, high‐resolution in vivo fluorescence imaging is achieved in the greater than 1300 nm window, and their good performance in photoacoustic imaging and high tumor PTT efficacy in tumor‐bearing mice are also demonstrated. Taken together, this work mainly provides a strong electron acceptor for constructing long‐emitting fluorophores, and by using the electron acceptor, a AIE fluorophore with desirable quantum yield (QY) and photothermal conversion efficienciy (PCE) is synthesized and demonstrated to be promising in fluorescence/photoacoustic imaging and PTT.https://doi.org/10.1002/agt2.458aggregation‐induced emissionfluorescence imagingphotoacoustic imagingphotothermal therapysecond near‐infrared fluorophores |
| spellingShingle | Mengke Liang Luyu Liu Ying Sun Jia Li Ling'e Zhang Xiqun Jiang Wei Wu Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy Aggregate aggregation‐induced emission fluorescence imaging photoacoustic imaging photothermal therapy second near‐infrared fluorophores |
| title | Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy |
| title_full | Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy |
| title_fullStr | Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy |
| title_full_unstemmed | Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy |
| title_short | Furan‐modified thiadiazolo quinoxaline as an electron acceptor for constructing second near‐infrared aggregation‐induced emission fluorophores for beyond 1300 nm fluorescence/photoacoustic imaging and photothermal therapy |
| title_sort | furan modified thiadiazolo quinoxaline as an electron acceptor for constructing second near infrared aggregation induced emission fluorophores for beyond 1300 nm fluorescence photoacoustic imaging and photothermal therapy |
| topic | aggregation‐induced emission fluorescence imaging photoacoustic imaging photothermal therapy second near‐infrared fluorophores |
| url | https://doi.org/10.1002/agt2.458 |
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