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] DPP has high stability to heat but not to acid and base. The alkylation of amide groups improves their solubility.

DPP-based pigments have been commercialized, e.g., C.I. Pigment Red 254. They have been used in automotive paints due to their high resistance to photodegradation.[4]

Structure

DPP dyes are based on the bicyclic heterocyclic compound diketopyrrolopyrrole. 2,5-Dihydropyrrolo[3,4-c]pyrrole-1,4-dione is a basic body of diketopyrrolopyrroles. Because of their low solubility they are difficult to process, but soluble derivatives, so called latent pigments, are soluble can be converted to DPP by thermolysis of solution deposited thin films.[5]

Optical properties

In addition to their use in inks, paints, and plastic, DPPs have attracted attention for optical-electronic properties, foreshadowing potential photovoltaic applications.[6] Modified DDP's show 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 investigated as fluorescent sensors, in organic solar cells.[12][13]

Research

DPP derivatives have been also investigated as promising fluorescent dyes for bioimaging applications,[14] as well as components of materials for use in organic electronics.[15][16][3][17]

DPPs are structurally related to other classes of dyes and pigments that feature cross-conjugated nitrogen atoms and carbonyl groups, including:

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. ^ a b 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. ^ Hunger, Klaus; Herbst, Willy (2000). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a20_371. ISBN 978-3-527-30385-4.
  5. ^ Zambounis, J. S.; Hao, Z.; Iqbal, A. (1997). "Latent pigments activated by heat". Nature. 388 (6638): 131–132. doi:10.1038/40532.
  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.
  12. ^ Patil, Yuvraj; Misra, Rajneesh (2019-10-31). "Rational molecular design towards NIR absorption: efficient diketopyrrolopyrrole derivatives for organic solar cells and photothermal therapy". Journal of Materials Chemistry C. 7 (42): 13020–13031. doi:10.1039/C9TC03640G. ISSN 2050-7534. S2CID 203513134.
  13. ^ Patil, Yuvraj; Misra, Rajneesh (June 2020). "Metal Functionalized Diketopyrrolopyrroles: A Promising Class of Materials for Optoelectronic Applications". The Chemical Record. 20 (6): 596–603. doi:10.1002/tcr.201900061. ISSN 1527-8999. PMID 31833617. S2CID 209340212.
  14. ^ 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.
  15. ^ Khan, Faizal; Jang, Youngwoo; Patil, Yuvraj; Misra, Rajneesh; D'Souza, Francis (2021-09-06). "Photoinduced Charge Separation Prompted Intervalence Charge Transfer in a Bis(thienyl)diketopyrrolopyrrole Bridged Donor-TCBD Push-Pull System". Angewandte Chemie International Edition. 60 (37): 20518–20527. doi:10.1002/anie.202108293. ISSN 1433-7851. PMID 34258866. S2CID 235820925.
  16. ^ Popli, Charu; Jang, Youngwoo; Patil, Yuvraj; Misra, Rajneesh; D'Souza, Francis (2020-11-26). "Formation of Highly Efficient, Long-Lived Charge Separated States in Star-Shaped Ferrocene-Diketopyrrolopyrrole-Triphenylamine Donor–Acceptor–Donor Conjugates". Chemistry: A European Journal. 26 (66): 15109–15115. doi:10.1002/chem.202002851. ISSN 0947-6539. PMID 32589288. S2CID 220075391.
  17. ^ 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. Bibcode:2013AdM....25.1859N. doi:10.1002/adma.201201795. hdl:10044/1/14443. ISSN 1521-4095. PMID 23008141. S2CID 10575133.

Further reading

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