DataVXAdvanced Optical MaterialsPaper
journal article·2016-05Open access

Biocompatible Two‐Photon Absorbing Dipyridyldiketopyrrolopyrroles for Metal‐Ion‐Mediated Self‐Assembly Modulation and Fluorescence Imaging

Tingchao He, Yang Gao, Sivaramapanicker Sreejith, Xiaoqing Tian, Lin Liu, Yue Wang, Hrishikesh Joshi, Soo Zeng Fiona Phua, Song Yao, Xiaodong Lin, Yanli Zhao, Andrew C. Grimsdale, Handong Sun

Advanced Optical Materials· Volume 4· Issue 5
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Source abstract

Abstract

Diketopyrrolopyrrole (DPP) derivatives are very promising nonlinear optical dyes with excellent thermal resistance and light stability. However, to the best of our knowledge, the fabrication of their organic micro‐ and/or nanostructures through covalent and/or noncovalent interactions to further adjust their corresponding two‐photon absorption (TPA) is rarely reported. In this work, based on previous synthesis method of pyridine‐containing ketopyrrolopyrroles, three dipyridyldiketopyrrolopyrroles (dipyridylDPPs) 1, 2, and 3 containing 2‐, 3‐, and 4‐pyridyl substituents, respectively, have been prepared, which exhibit strong orange fluorescence and large TPA action cross‐sections in both organic (tetrahydrofuran) and aqueous media. Importantly, fluorescent organic nanoparticles (FONs) of the di(2‐pyridyl)DPP 1 prepared by the reprecipitation method displays strong two‐photon emission. Meanwhile, the FONs of 1 not only exhibit Ag+ ions mediated self‐assembly modulation, but also display low cytotoxicity and allow two‐photon bioimaging in HeLa cells.
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Research context

NanomaterialsBiomaterials

OpenAlex topics: Nonlinear Optical Materials Studies · Luminescence and Fluorescent Materials · Porphyrin and Phthalocyanine Chemistry

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

College of Physics Science & Technology Shenzhen University Shenzhen 518060 China

School of Materials Science and Engineering Nanyang Technological University 50 Nanyang Avenue 639798 Singapore

Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link 637371 Singapore

Division of Physics and Applied Physics and Centre for Disruptive Photonic Technologies (CDPT) School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link 637371 Singapore

Funding

Natural Science Foundation of China · Natural Science Foundation of Guangdong Province · Youth Innovation Talent Project (Nature Science) of the Universities of Guangdong Province · Shenzhen Basic Research Project of Science and Technology · Shanghai Jiao Tong University, China

References (41)

Show source-provided references
1. 10.1021/cr500442510.1021/cr5004425 ↗
2. 10.1039/C4CS00372A10.1039/C4CS00372A ↗
3. 10.1039/C4OB00431K10.1039/C4OB00431K ↗
4. 10.1364/JOSAB.13.00048110.1364/JOSAB.13.000481 ↗
5. 10.1021/jo502775t10.1021/jo502775t ↗
6. 10.1002/chem.20120261310.1002/chem.201202613 ↗
7. 10.1021/jacs.5b0354810.1021/jacs.5b03548 ↗
8. 10.1002/anie.20120610710.1002/anie.201206107 ↗
9. 10.1021/cr050054x10.1021/cr050054x ↗
10. 10.1126/science.281.5383.165310.1126/science.281.5383.1653 ↗
11. 10.1002/anie.20080525710.1002/anie.200805257 ↗
12. 10.1002/asia.20120100910.1002/asia.201201009 ↗
13. 10.1016/j.tet.2014.01.03210.1016/j.tet.2014.01.032 ↗
14. 10.1002/adma.20130460210.1002/adma.201304602 ↗
15. 10.1002/smll.20110072610.1002/smll.201100726 ↗
16. 10.1002/adom.20140055910.1002/adom.201400559 ↗
17. 10.1039/C4CS00248B10.1039/C4CS00248B ↗
18. 10.1039/b911808j10.1039/b911808j ↗
19. 10.1002/chem.20150073810.1002/chem.201500738 ↗
20. 10.1002/anie.20140753710.1002/anie.201407537 ↗
21. 10.1039/C4TC02375G10.1039/C4TC02375G ↗
22. 10.1002/adfm.20150001010.1002/adfm.201500010 ↗
23. Kimw H. M. · Chem. Commun. · 2009 · 45 · 153
24. 10.1016/j.dyepig.2012.11.02810.1016/j.dyepig.2012.11.028 ↗
25. 10.1016/j.dyepig.2005.01.00110.1016/j.dyepig.2005.01.001 ↗
26. 10.1021/ar900233v10.1021/ar900233v ↗
27. 10.1039/C4CC02564D10.1039/C4CC02564D ↗
28. 10.1002/anie.20141004110.1002/anie.201410041 ↗
29. 10.1002/adfm.20060091610.1002/adfm.200600916 ↗
30. 10.1002/asia.20120019210.1002/asia.201200192 ↗
31. 10.1021/acsami.5b0022310.1021/acsami.5b00223 ↗
32. 10.1002/anie.20080525710.1002/anie.200805257 ↗
33. 10.1021/acs.jpcc.5b0094010.1021/acs.jpcc.5b00940 ↗
34. 10.1039/C4CC05999A10.1039/C4CC05999A ↗
35. 10.1002/978047046733610.1002/9780470467336 ↗
36. 10.1021/ja049013t10.1021/ja049013t ↗
37. 10.1039/b905571a10.1039/b905571a ↗
38. 10.1021/jo049124a10.1021/jo049124a ↗
39. 10.1016/j.molstruc.2010.08.02610.1016/j.molstruc.2010.08.026 ↗
40. 10.1039/c3cc44676j10.1039/c3cc44676j ↗
41. 10.1002/adma.20140008410.1002/adma.201400084 ↗