Diketopyrrolopyrrole dye

Diketopyrrolopyrroles (DPPs) are organic dyes and pigments based on the heterocyclic dilactam 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione.[1][2][3] DPPs were initially used as pigments in the painting industry (e.g. in automotive paints) due to their high resistance to photodegradation. More recently, DPP derivatives have been also investigated as promising fluorescent dyes for bioimaging applications,[4] as well as components of materials for use in organic electronics.[3][5]

Structure
nomenclature

DPP dyes are based on the bicyclic heterocyclic compound diketopyrrolopyrrole. 2,5-Dihydropyrrolo[3,4-c]pyrrol-1,4-dion is a basic body of Diketopyrrolopyrrole dye. DPP pigments are an important class of high-performance pigments used in inks, paints and plastic. More recently their optical-electronic performance was discovered for photovoltaic applications and related uses.[6]

Optical properties

DPP has high stability to heat but not very well to acid and base. The alkylation of amide groups improves the solubility. The modified DDP shows high fluorescence and the emission wavelength is adjustable by change the aromatic group at 3 and 6 positions. Both electron donor group, such as thiophene, and expanding of the conjugated system increase the emission wavelength. DPP is also developed as a red emitting group in pure polymer light emitting diodes.[7][8][9][10] Some DPP derivatives show aggregation induced emission[11] and were used as effective fluorescent sensors.

References
  1. Wallquist, O.; Lenz, R. (2002-03-01). "DPP chemistry — continuous innovation". Surface Coatings International Part B: Coatings Transactions. 85 (1): 19–26. doi:10.1007/BF02699738. ISSN 1476-4865. S2CID 98773045.
  2. Grzybowski, Marek; Gryko, Daniel T. (2015). "Diketopyrrolopyrroles: Synthesis, Reactivity, and Optical Properties". Advanced Optical Materials. 3 (3): 280–320. doi:10.1002/adom.201400559. ISSN 2195-1071.
  3. Tian, He; Qu, Sanyin (2012-02-27). "Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics". Chemical Communications. 48 (25): 3039–3051. doi:10.1039/C2CC17886A. ISSN 1364-548X. PMID 22343975.
  4. Choi, Dong Hoon; Kaur, Matinder (2014-12-08). "Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications". Chemical Society Reviews. 44 (1): 58–77. doi:10.1039/C4CS00248B. ISSN 1460-4744. PMID 25186723.
  5. Nielsen, Christian B.; Turbiez, Mathieu; McCulloch, Iain (2013). "Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications" (PDF). Advanced Materials. 25 (13): 1859–1880. doi:10.1002/adma.201201795. hdl:10044/1/14443. ISSN 1521-4095. PMID 23008141.
  6. Encyclopedia of Interfacial Chemistry: Surface Science and Electrochemistry. Elsevier. 2018-03-29. ISBN 978-0-12-809894-3.
  7. Jin, Yi; Xu, Yanbin; Qiao, Zhi; Peng, Junbiao; Wang, Baozheng; Cao, Derong (2010). "Enhancement of Electroluminescence Properties of Red Diketopyrrolopyrrole-Doped Copolymers by Oxadiazole and Carbazole Units as Pendants". Polymer. 51 (24): 5726–5733. doi:10.1016/j.polymer.2010.09.046.
  8. Qiao, Zhi; Peng, Junbiao; Jin, Yi; Liu, Qilin; Weng, Jiena; He, Zhicai; Han, Shaohu; Cao, Derong (2010). "Synthesis and Electroluminescence Properties of Fluorene-co-Diketopyrrolopyrrole-co-Phenothiazine Polymers". Polymer. 51 (5): 1016–1023. doi:10.1016/j.polymer.2009.12.044.
  9. Xu, Yanbin; Jin, Yi; Lin, Weihong; Peng, Junbiao; Jiang, Huanfeng; Cao, Derong (2010). "Syntheses and Electroluminescence Properties of Red Emitting Copolymers with Different Lengths of Diketopyrrolopyrrole Units". Synthetic Metals. 160 (19–20): 2135–2142. doi:10.1016/j.synthmet.2010.07.044.
  10. Xu, Yanbin; Jin, Yi; Peng, Junbiao; Wang, Baozheng; Cao, Derong (2010). "Syntheses and Characterization of 4-Octyloxybenzyl Substituted Diketopyrrolopyrrole-Based Red Emitting Copolymers with Low Turn-on Voltage". J. Macromol. Sci., Part A: Pure Appl. Chem. 47 (11): 1059–1068. doi:10.1080/10601325.2010.511091. S2CID 97899350.
  11. Jin, Yi; Xu, Yanbin; Liu, Yinling; Wang, Lingyun; Jiang, Huanfeng; Li, Xianjie; Cao, Derong (2011). "Synthesis of Novel Diketopyrrolopyrrole-Based Luminophores Showing Crystallization-Induced Emission Enhancement Properties". Dyes Pigm. 90 (3): 311–318. doi:10.1016/j.dyepig.2011.01.005.

Further reading
  • Chem. Commun., 2012, 48, 3039–3051
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