Conformationally confined three-armed supramolecular folding for boosting near-infrared biological imaging
Herein, a triphenylamine derivative ( TP-3PY ) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ p -(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the vis...
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Published in | Chemical science (Cambridge) Vol. 14; no. 31; pp. 841 - 847 |
---|---|
Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
09.08.2023
The Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
ISSN | 2041-6520 2041-6539 |
DOI | 10.1039/d3sc02599c |
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Abstract | Herein, a triphenylamine derivative (
TP-3PY
) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[
p
-(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region (
λ
max
= 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]),
TP-3PY
showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (
TP-3PY
⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of
TP-3PY
was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of
TP-3PY
⊂CB[8]@SC4AD and
TP-3PY
⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice.
A conformation confined NIR photoluminescent supramolecular foldamer was constructed and used for lysosome-targeted imaging and real-time
in vivo
imaging of intact animals. |
---|---|
AbstractList | Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[
-(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region (
= 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ p -(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region ( λ max = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. A conformation confined NIR photoluminescent supramolecular foldamer was constructed and used for lysosome-targeted imaging and real-time in vivo imaging of intact animals. Herein, a triphenylamine derivative ( TP-3PY ) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ p -(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region ( λ max = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly ( TP-3PY ⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY ⊂CB[8]@SC4AD and TP-3PY ⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. A conformation confined NIR photoluminescent supramolecular foldamer was constructed and used for lysosome-targeted imaging and real-time in vivo imaging of intact animals. Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[p-(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region (λmax = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice.Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[p-(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region (λmax = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ p -(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region ( λ max = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[p-(4-pyridylvinyl)phenyl]amine (TPA) with large two-photon absorption cross-sections as an electron-donating group was obtained, and showed intense absorption in the visible light region (λmax = 509 nm) and weak near-infrared (NIR) fluorescence emission at 750 nm. After complexation with cucurbit[8]uril (CB[8]), TP-3PY showed bright NIR fluorescence emission at 727 nm and phosphorescence emission at 800 nm. When the supramolecular assembly (TP-3PY⊂CB[8]) further interacted with dodecyl-modified sulfonatocalix[4]arene (SC4AD), the fluorescence and phosphorescence emissions were further enhanced at 710 and 734 nm, respectively. However, only the fluorescence emission of TP-3PY was enhanced in the presence of cucurbit[7]uril (CB[7]) and SC4AD. More interestingly, the photoluminescence of TP-3PY⊂CB[8]@SC4AD and TP-3PY⊂CB[7]@SC4AD assemblies could be excited by both visible (510 nm) and NIR light (930 nm). Finally, these ternary supramolecular assemblies with bright NIR light emission were applied to lysosome imaging of tumor cells and real-time biological imaging of mice. |
Author | Li, Yong-Xue Yu, Qilin Wang, Hui-Juan Zheng, Meng-Meng Liu, Yu Zhu, Hongjie Zhang, Ying-Ming Xing, Wen-Wen Wang, Yao-Yao |
AuthorAffiliation | Haihe Laboratory of Sustainable Chemical Transformations (Tianjin) Nankai University College of Chemistry Key Laboratory of Molecular Microbiology and Technology College of Life Sciences State Key Laboratory of Elemento-Organic Chemistry Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology School of Chemistry and Chemical Engineering Liaocheng University Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) |
AuthorAffiliation_xml | – sequence: 0 name: Haihe Laboratory of Sustainable Chemical Transformations (Tianjin) – sequence: 0 name: Liaocheng University – sequence: 0 name: Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) – sequence: 0 name: College of Chemistry – sequence: 0 name: School of Chemistry and Chemical Engineering – sequence: 0 name: Nankai University – sequence: 0 name: Key Laboratory of Molecular Microbiology and Technology – sequence: 0 name: College of Life Sciences – sequence: 0 name: State Key Laboratory of Elemento-Organic Chemistry – sequence: 0 name: Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology |
Author_xml | – sequence: 1 givenname: Hui-Juan surname: Wang fullname: Wang, Hui-Juan – sequence: 2 givenname: Meng-Meng surname: Zheng fullname: Zheng, Meng-Meng – sequence: 3 givenname: Wen-Wen surname: Xing fullname: Xing, Wen-Wen – sequence: 4 givenname: Yong-Xue surname: Li fullname: Li, Yong-Xue – sequence: 5 givenname: Yao-Yao surname: Wang fullname: Wang, Yao-Yao – sequence: 6 givenname: Hongjie surname: Zhu fullname: Zhu, Hongjie – sequence: 7 givenname: Ying-Ming surname: Zhang fullname: Zhang, Ying-Ming – sequence: 8 givenname: Qilin surname: Yu fullname: Yu, Qilin – sequence: 9 givenname: Yu surname: Liu fullname: Liu, Yu |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37564418$$D View this record in MEDLINE/PubMed |
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CitedBy_id | crossref_primary_10_1039_D3SC06349F crossref_primary_10_1007_s11426_024_1971_4 crossref_primary_10_1039_D4NJ01843E crossref_primary_10_1016_j_cclet_2023_109183 crossref_primary_10_1016_j_cej_2025_161092 crossref_primary_10_1007_s12274_024_6906_0 crossref_primary_10_1016_j_ccr_2025_216555 crossref_primary_10_1039_D4MH00873A crossref_primary_10_1002_agt2_562 |
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Snippet | Herein, a triphenylamine derivative (
TP-3PY
) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[
p... Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ p -(4-pyridylvinyl)phenyl]amine... Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[ -(4-pyridylvinyl)phenyl]amine... Herein, a triphenylamine derivative (TP-3PY) possessing 4-(4-bromophenyl)pyridine (PY) as an electron-accepting group and tris[p-(4-pyridylvinyl)phenyl]amine... |
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SubjectTerms | Absorption cross sections Assemblies Chemistry Fluorescence Infrared imaging Light emission Near infrared radiation Phosphorescence Photoluminescence Photon absorption |
Title | Conformationally confined three-armed supramolecular folding for boosting near-infrared biological imaging |
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