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Brilliant red or orange high performance pigments Brilliant red or orange high performance pigments Extremely: Extremely: Insoluble Insoluble Resistant.

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Presentation on theme: "Brilliant red or orange high performance pigments Brilliant red or orange high performance pigments Extremely: Extremely: Insoluble Insoluble Resistant."— Presentation transcript:

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2 Brilliant red or orange high performance pigments Brilliant red or orange high performance pigments Extremely: Extremely: Insoluble Insoluble Resistant (ΔT, hν, etc.) Resistant (ΔT, hν, etc.) Used in: Used in: Luxury cars painting Luxury cars painting High quality printing High quality printing Plastics coloring Plastics coloring Solar cells, OLED, Fluorescence imaging etc. Solar cells, OLED, Fluorescence imaging etc.

3 1974 – Farnum et al – accidental discovery of DPP 1 1. Farnum D G, Mehta G, Moore G G I, Siegal F P, Tetrahedron Lett. 1974, 15, %

4 1983 – Iqbal and Cassar patent 2 : Synthesis of DPP by condensation of succinate with aromatic nitrile R 1, R 2 = iPr, tBu, tAm etc. 2. Iqbal A, Cassar L, Ciba-Geigy Ltd, US Patent 4, 1983, 415, %

5 Reason: Strong molecular interactions 3,4 3. Lenz R, Wallquist O, Surface Coatings International Part B: Coatings Transactions, 2002, 85, 1-xxx 4. Mizuguchi J, Grubenmann A, Wooden G, Rihs G, Acta Crystallographica, Section B, 1992, 48, 696 1,82Å 7°

6 Reason: Strong molecular interactions 3,4 3,5Å 3. Lenz R, Wallquist O, Surface Coatings International Part B: Coatings Transactions, 2002, 85, 1-xxx 4. Mizuguchi J, Grubenmann A, Wooden G, Rihs G, Acta Crystallographica, Section B, 1992, 48, 696

7 Heat fastness: < 500°C Heat fastness: < 500°C 8th grade light resistance (1 to 8 scale) 8th grade light resistance (1 to 8 scale) ε > M -1 · cm -1 ε > M -1 · cm -1 Low Stokes shift < 30 nm (< 0,75 eV) usually ~12-15 nm Low Stokes shift < 30 nm (< 0,75 eV) usually ~12-15 nm λ max : nm λ max : nm Hypsochromic shift in solution Hypsochromic shift in solution Fluorescence quantum yield ~0,5 Fluorescence quantum yield ~0,5 110 mg dissolves in 1L of DMF 110 mg dissolves in 1L of DMF

8 5. Industrial Organic Pigments, Herbst W, Hunger K, WILEY-VCH, Weinheim, 2004, p Ciba was selling this for $100 per kilo, and the cost was $20 per kilo, so it was a big advantage for the company 6Ciba was selling this for $100 per kilo, and the cost was $20 per kilo, so it was a big advantage for the company 6

9 Latent pigment 6. Zambounis J, Hao Z, Iqbal A, Nature, 1997, 388, 131

10 Larger/More branched substituent = Better solubility Larger/More branched substituent = Better solubility Φ F increases up to 0,9 Φ F increases up to 0,9 Stokes shift up to 70 nm (~2 eV) Stokes shift up to 70 nm (~2 eV) Lower temperature resistance (<300°C) Lower temperature resistance (<300°C) 7. Colonna G, Pilati T, Rusconi F, Zecchi G, Dyes and Pigments, 2007, 75, 125 Alcoxides and hydroxides were also used as bases 5-90 % 7

11 Fluorescence imaging Fluorescence imaging Electroluminescence Electroluminescence Solar cells Solar cells Conductive polymers Conductive polymers Photoconductive materials Photoconductive materials Two photon absorption Two photon absorption Ions and molecules fluorescent sernsors Ions and molecules fluorescent sernsors Laser dyes Laser dyes Optical data storage Optical data storage Liquid crystals Liquid crystals Electrochromic materials Electrochromic materials Field effect transistors Field effect transistors 8. High Performance Pigments, Faulkner E B, Schwartz R J, WILEY-VCH, Weinheim, 2009, p.191

12 9. Guo E Q, Ren P H, Zhang Y L, Zhang H C, Yang W J, Chem. Commun., 2009, 2859

13 Compound λ abs /nm λ em /nm Δν/nm Φ λ 2PA /nm δ max /GM δ max /MW DPP-R , ,31 DPP-DPA , ,98 DPP-TPA , ,68

14 10. Jiang Y, Wang Y, Hua J, Qu S, Qian S, Tian H, J. Polym. Sci.: Part A: Polymer Chemistry, 2009, 47, 4400

15 11. Yamagata T, Kuwabara J, Kanbara T, Tetrahedron Lett., 2010, 51, HCOOH2 + TFA

16 11. Yamagata T, Kuwabara J, Kanbara T, Tetrahedron Lett., 2010, 51, – 1000 eq of TFA 1250 – 5000 eq of TFA 2 in CHCl 3 (2 · M)

17 12. Qu Y, Hua J, Tian H, Org. Lett., 2010, 12, 3320Compound-Ar1 2 3

18 13. Fisher G M, Jüngst Ch, Isomäki-Krondahl M, Gauss D, Möller H M, Daltrozzo E, Zumbusch A, Chem. Comm., 2010, 46, Fischer G M, Ehlers A P, Zumbusch A, Daltrozzo E, Angew. Chem. Int. Ed., 2007, 46, Fischer G M, Daltrozzo E, Zumbusch A, Angew. Chem. Int. Ed., 2011, 50, Fischer G M, Isomäki-Krondahl M, Göttker-Schnetmann I, Daltrozzo E, Zumbusch A, Chem. Eur. J., 2009, 15, 4857 POCl 3 ε = – M -1 cm -1 λ abs = 684 – 864 nm λ em = 708 – 881 nm Φ F = 0,32 – 0,69

19 13. Fisher G M, Jüngst Ch, Isomäki-Krondahl M, Gauss D, Möller H M, Daltrozzo E, Zumbusch A, Chem. Comm., 2010, 46, Fischer G M, Ehlers A P, Zumbusch A, Daltrozzo E, Angew. Chem. Int. Ed., 2007, 46, Fischer G M, Daltrozzo E, Zumbusch A, Angew. Chem. Int. Ed., 2011, 50, Fischer G M, Isomäki-Krondahl M, Göttker-Schnetmann I, Daltrozzo E, Zumbusch A, Chem. Eur. J., 2009, 15, 4857

20 17. Prashant S, Ging-Meng N, Ting Ting L, Ananth D, Zhi-Kuan C, J. Mater. Chem., 2010, 20, 3626 Electrochemical bangap: 1,63 – 1,74 eV 1% power conversion for TFPDPP

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