{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T06:19:53Z","timestamp":1777529993237,"version":"3.51.4"},"reference-count":38,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2022,5,6]],"date-time":"2022-05-06T00:00:00Z","timestamp":1651795200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003695","name":"Korea Institute of Industrial Technology","doi-asserted-by":"publisher","award":["kitech EO-22-0002"],"award-info":[{"award-number":["kitech EO-22-0002"]}],"id":[{"id":"10.13039\/501100003695","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Conventional fluorescent dyes have the property of decreasing fluorescence due to aggregation-caused quenching effects at high concentrations, whereas aggregation-induced emission dyes have the property of increasing fluorescence as they aggregate with each other. In this study, diketopyrrolopyrrole-based long-wavelength aggregation-induced emission dyes were used to prepare biocompatible nanoparticles suitable for bioimaging. Aggregation-induced emission nanoparticles with the best morphology and photoluminescence intensity were obtained through a fast, simple preparation method using an ultrasonicator. The optimally prepared nanoparticles from 3,6-bis(4-((E)-4-(bis(40-(1,2,2-triphenylvinyl)-[1,10-biphenyl]-4-yl)amino)styryl)phenyl)-2,5-dihexyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DP-R2) with two functional groups having aggregation-induced emission properties and additional donating groups at the end of the triphenylamine groups were considered to have the greatest potential as a fluorescent probe for bioimaging. Furthermore, it was found that the tendency for aggregation-induced emission, which was apparent for the dye itself, became much more marked after the dyes were incorporated within nanoparticles. While the photoluminescence intensities of the dyes were observed to decrease rapidly over time, the prepared nanoparticles encapsulated within the biocompatible polymers maintained their initial optical properties very well. Lastly, when the cell viability test was conducted, excellent biocompatibility was demonstrated for each of the prepared nanoparticles.<\/jats:p>","DOI":"10.3390\/molecules27092984","type":"journal-article","created":{"date-parts":[[2022,5,8]],"date-time":"2022-05-08T21:31:20Z","timestamp":1652045480000},"page":"2984","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis and Characterization of Diketopyrrolopyrrole-Based Aggregation-Induced Emission Nanoparticles for Bioimaging"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8509-5819","authenticated-orcid":false,"given":"Geonho","family":"Lee","sequence":"first","affiliation":[{"name":"Material & Component Convergence R&D Department, Korea Institute of Industrial Technology (KITECH), Ansan 15588, Korea"},{"name":"Department of Chemical Engineering, KyungHee University, Yongin 17104, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jongwook","family":"Park","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, KyungHee University, Yongin 17104, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seong Hyun","family":"Jang","sequence":"additional","affiliation":[{"name":"Material & Component Convergence R&D Department, Korea Institute of Industrial Technology (KITECH), Ansan 15588, Korea"},{"name":"Laboratory of Organic Photo-Functional Materials, Department of Materials Science and Engineering, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sang Yoon","family":"Lee","sequence":"additional","affiliation":[{"name":"Material & Component Convergence R&D Department, Korea Institute of Industrial Technology (KITECH), Ansan 15588, Korea"},{"name":"Department of Advanced Materials Engineering for Information & Electronics, Integrated Education Institute for Frontier Science & Technology BK21 Four, KyungHee University, Yongin 17104, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jihyun","family":"Seong","sequence":"additional","affiliation":[{"name":"Department of Chemical and Biochemical Engineering, Dongguk University, Seoul 04620, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2473-0222","authenticated-orcid":false,"given":"Jae Woong","family":"Jung","sequence":"additional","affiliation":[{"name":"Department of Advanced Materials Engineering for Information & Electronics, Integrated Education Institute for Frontier Science & Technology BK21 Four, KyungHee University, Yongin 17104, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3678-2078","authenticated-orcid":false,"given":"Kyobum","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemical and Biochemical Engineering, Dongguk University, Seoul 04620, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tae Gyu","family":"Hwang","sequence":"additional","affiliation":[{"name":"Research Center for Advanced Specialty Chemicals, Korea Research Institute of Chemical Technology (KRICT), Ulsan 44412, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jun","family":"Choi","sequence":"additional","affiliation":[{"name":"Material & Component Convergence R&D Department, Korea Institute of Industrial Technology (KITECH), Ansan 15588, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1002\/pi.1974","article-title":"Organic light-emitting diode (OLED) technology: Materials, devices and display technologies","volume":"55","author":"Geffroy","year":"2006","journal-title":"Polym. Int."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"104271","DOI":"10.1016\/j.nanoen.2019.104271","article-title":"Regulating the phase separation of ternary organic solar cells via 3D architectured AIE molecules","volume":"68","author":"Adil","year":"2020","journal-title":"Nano Energy"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1021\/acs.jpclett.6b02378","article-title":"Entangled photon excited fluorescence in organic materials: An ultrafast coincidence detector","volume":"8","author":"Varnavski","year":"2017","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2471","DOI":"10.1039\/C5NR05051K","article-title":"Fluorescent nanoparticles based on AIE fluorogens for bioimaging","volume":"8","author":"Yan","year":"2016","journal-title":"Nanoscale"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.chempr.2017.05.010","article-title":"AIE luminogens for bioimaging and theranostics: From organelles to animals","volume":"3","author":"Qian","year":"2017","journal-title":"Chem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4228","DOI":"10.1039\/C4CS00325J","article-title":"Biosensing by luminogens with aggregation-induced emission characteristics","volume":"44","author":"Kwok","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1006\/bbrc.2001.4404","article-title":"Nondestructive quantification of neutral lipids by thin-layer chromatography and laser-fluorescent scanning: Suitable methods for \u201clipidome\u201d analysis","volume":"281","author":"Kishimoto","year":"2001","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1126\/science.265.5173.765","article-title":"Excimers and exciplexes of conjugated polymers","volume":"265","author":"Jenekhe","year":"1994","journal-title":"Science"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2974","DOI":"10.1039\/b102221k","article-title":"Efficient blue emission from siloles","volume":"11","author":"Tang","year":"2001","journal-title":"J. Mater. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1740","DOI":"10.1039\/b105159h","article-title":"Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole","volume":"18","author":"Luo","year":"2001","journal-title":"Chem. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"428","DOI":"10.1039\/C8MH01331D","article-title":"Aggregation-induced emission: Fundamental understanding and future developments","volume":"6","author":"Chen","year":"2019","journal-title":"Mater. Horiz."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1007\/s11426-018-9382-3","article-title":"Enhancement strategies of targetability, response and photostability for in vivo bioimaging","volume":"62","author":"Gu","year":"2019","journal-title":"Sci. China Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"16972","DOI":"10.1039\/C4RA16233A","article-title":"High-quality water-soluble luminescent carbon dots for multicolor patterning, sensors, and bioimaging","volume":"5","author":"Lu","year":"2015","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"32706","DOI":"10.1021\/acsami.6b12252","article-title":"Aspirin-based carbon dots, a good biocompatibility of material applied for bioimaging and anti-inflammation","volume":"8","author":"Xu","year":"2016","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1219","DOI":"10.1039\/C8SC04363A","article-title":"Novel near-infrared II aggregation-induced emission dots for in vivo bioimaging","volume":"10","author":"Lin","year":"2019","journal-title":"Chem. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1016\/j.jlumin.2018.03.032","article-title":"Proficient surface modification of CdSe quantum dots for highly luminescent and biocompatible probes for bioimaging: A comparative experimental investigation","volume":"199","author":"Kumari","year":"2018","journal-title":"J. Lumin."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.ejpb.2007.05.013","article-title":"Polymer coating of quantum dots\u2013a powerful tool toward diagnostics and sensorics","volume":"68","author":"Hezinger","year":"2008","journal-title":"Eur. J. Pharm. Biopharm."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1039\/C6MH00060F","article-title":"Fabrication of fluorescent nanoparticles based on AIE luminogens (AIE dots) and their applications in bioimaging","volume":"3","author":"Chen","year":"2016","journal-title":"Mater. Horiz."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"429","DOI":"10.1039\/C0NR00458H","article-title":"Biocompatible glutathione capped gold clusters as one-and two-photon excitation fluorescence contrast agents for live cells imaging","volume":"3","author":"Polavarapu","year":"2011","journal-title":"Nanoscale"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5951","DOI":"10.1021\/ac8005796","article-title":"Nonbleaching fluorescence of gold nanoparticles and its applications in cancer cell imaging","volume":"80","author":"He","year":"2008","journal-title":"Anal. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6267","DOI":"10.1039\/C8DT00420J","article-title":"Luminescence mechanisms of ultrasmall gold nanoparticles","volume":"47","author":"Huang","year":"2018","journal-title":"Dalton Trans."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1018","DOI":"10.1039\/C3CC47864E","article-title":"A near-infrared fluorescent probe for selective detection of HClO based on Se-sensitized aggregation of heptamethine cyanine dye","volume":"50","author":"Cheng","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1751","DOI":"10.1039\/c3cc48128j","article-title":"A near-infrared colorimetric fluorescent chemodosimeter for the detection of glutathione in living cells","volume":"50","author":"Li","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"0010","DOI":"10.1038\/s41551-016-0010","article-title":"Near-infrared fluorophores for biomedical imaging","volume":"1","author":"Hong","year":"2017","journal-title":"Nat. Biomed. Eng."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4205","DOI":"10.1248\/cpb.32.4205","article-title":"Pluronic F-127 gels as a vehicle for topical administration of anticancer agents","volume":"32","author":"Miyazaki","year":"1984","journal-title":"Chem. Pharm. Bull."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1791","DOI":"10.1002\/marc.201200329","article-title":"Preparation, cellular internalization, and biocompatibility of highly fluorescent PMMA nanoparticles","volume":"33","author":"Vollrath","year":"2012","journal-title":"Macromol. Rapid Commun."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/j.jphotobiol.2004.01.002","article-title":"Enhanced photo-stability, thermal-stability and aqueous-stability of indocyanine green in polymeric nanoparticulate systems","volume":"74","author":"Saxena","year":"2004","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"5603","DOI":"10.1016\/j.biomaterials.2012.04.044","article-title":"Indocyanine green-loaded biodegradable tumor targeting nanoprobes for in vitro and in vivo imaging","volume":"33","author":"Zheng","year":"2012","journal-title":"Biomaterials"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"15888","DOI":"10.1021\/acssuschemeng.0c04456","article-title":"Enhancement of Lipid Productivity of Chlorella sp. Using Light-Converting Red Fluorescent Films Based on Aggregation-Induced Emission","volume":"8","author":"Hwang","year":"2020","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5859","DOI":"10.1039\/b911808j","article-title":"Diphenylamine end-capped 1,4-diketo-3,6-diphenylpyrrolo [3,4-c] pyrrole (DPP) derivatives with large two-photon absorption cross-sections and strong two-photon excitation red fluorescence","volume":"39","author":"Guo","year":"2009","journal-title":"Chem. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1016\/j.dyepig.2016.05.043","article-title":"Tetraphenylethene end-capped diketopyrrolopyrrole fluorogens with AIE and large two-photon absorption cross-sections features and application in bioimaging","volume":"133","author":"Jiang","year":"2016","journal-title":"Dye. Pigment."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5205","DOI":"10.1039\/D1SE00638J","article-title":"Highly efficient light-converting films based on diketopyrrolopyrrole with deep-red aggregation-induced emission for enhancing the lipid productivity of Chlorella sp.","volume":"5","author":"Hwang","year":"2021","journal-title":"Sustain. Energy Fuels"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/j.bios.2019.04.023","article-title":"Ultrabright fluorescent microsphere and its novel application for improving the sensitivity of immunochromatographic assay","volume":"135","author":"Zhang","year":"2019","journal-title":"Biosens. Bioelectron."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"784","DOI":"10.1039\/C4CC07451C","article-title":"Aggregation-induced emission (AIE) of pyridyl-enamido-based organoboron luminophores","volume":"51","author":"Wang","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1255","DOI":"10.1038\/s41467-020-15095-1","article-title":"Design of AIEgens for near-infrared IIb imaging through structural modulation at molecular and morphological levels","volume":"11","author":"Li","year":"2020","journal-title":"Nat. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6303","DOI":"10.1039\/b815431g","article-title":"An aggregation-induced blue shift of emission and the self-assembly of nanoparticles from a novel amphiphilic oligofluorene","volume":"47","author":"Zhu","year":"2008","journal-title":"Chem. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"527","DOI":"10.1016\/j.jcis.2009.07.033","article-title":"Aggregation-induced blue shift of fluorescence emission due to suppression of TICT in a phenothiazine-based organogel","volume":"339","author":"Yang","year":"2009","journal-title":"J. Colloid Interface Sci."},{"key":"ref_38","first-page":"87","article-title":"Biosynthesis and characterization of biogenic tellurium nanoparticles by using Penicillium chrysogenum PTCC 5031: A novel approach in gold biotechnology","volume":"17","author":"Barabadi","year":"2018","journal-title":"Iran. J. Pharm. Res."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/9\/2984\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:07:07Z","timestamp":1760137627000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/9\/2984"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,6]]},"references-count":38,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["molecules27092984"],"URL":"https:\/\/doi.org\/10.3390\/molecules27092984","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,6]]}}}