Panchromatic Push–Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules

Elodie Heyer; Raymond Ziessel

doi:10.1055/s-0034-1378818

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(15): 2109-2116
DOI: 10.1055/s-0034-1378818

letter

Panchromatic Push–Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules

Elodie Heyer

Institut de Chimie et Procédés pour l’Energie, l’Environnement et la Santé (ICPEES), Laboratoire de Chimie Organique et Spectroscopies Avancées (LCOSA), Université de Strasbourg/CNRS (UMR 7515), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg, France eMail: ziessel@unistra.fr

,

Raymond Ziessel*

Institut de Chimie et Procédés pour l’Energie, l’Environnement et la Santé (ICPEES), Laboratoire de Chimie Organique et Spectroscopies Avancées (LCOSA), Université de Strasbourg/CNRS (UMR 7515), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087 Strasbourg, France eMail: ziessel@unistra.fr

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Abstract

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Abstract

Several symmetrical and unsymmetrical thiophene-functionalized diketopyrrolopyrrole chromophores bearing a bis(p-methoxyphenyl)-p-phenylamine substituent were synthesized through palladium-catalyzed cross-coupling reactions. Mono-substitution and di-substitution occur using either alkyne or borolane groups, allowing the preparation of mixed systems. The alkyne derivatives could be prepared in high yields, and are versatile building blocks for the [2+2] cycloaddition of tetracyanoethylene, leading to 1,1,4,4-tetracyanobuta-1,3-diene derivatives. These interesting push–pull molecules exhibit a rich redox activity, which is understandable in light of the behavior of appropriate reference compounds. These innovative and rationally designed scaffolds are highly colored, exhibiting high absorption coefficients and spanning an absorption range of more than 600 nm of the UV/Vis electromagnetic spectrum.

Key words

cross-coupling reactions - cycloaddition reactions - push–pull molecules - panchromatic dyes - redox properties

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References and Notes

1a Blanchard-Desce M, Alain V, Bedworth PV, Marder SR, Fort A, Runser C, Barzoukas M, Lebus S, Wortmann R. Chem. Eur. J. 1997; 3: 1091
1b Kanis DR, Ratner MA, Marks TJ. Chem. Rev. 1994; 94: 195
1c Dalton LR, Sullivan PA, Bale DH. Chem. Rev. 2010; 110: 25

2a So PT. C, Dong CY, Masters BR, Berland KM. Annu. Rev. Biomed. Eng. 2000; 2: 399
2b Geiger FM. Annu. Rev. Phys. Chem. 2009; 60: 61

3 Bürckstümmer H, Tulyakova EV, Deppisch M, Lenze MR, Kronenberg NM, Gsaänger M, Stolote M, Meerholz K, Würthner F. Angew. Chem. Int. Ed. 2011; 50: 11628

4a Chou Y.-H, Chang H.-C, Liu C.-L, Chen W.-C. Polymer. Chem. 2015; 6: 341
4b Lei T, Wang J.-Y, Pei J. Acc. Chem. Res. 2014; 47: 1117

5 Ning Z, Tian H. Chem. Commun. 2009; 37: 5483

6a Cha H, Kim HN, An TK, Kang MS, Kwon S.-K, Kim Y.-H, Park CE. Appl. Mater. Inter. 2014; 6: 15774
6b Cha H, Kim HN, An TK, Kang MS, Kwon S.-K, Kim Y.-H, Park CE. Appl. Mater. Inter. 2014; 6: 15774

7a Hao Z, Iqbal A. Chem. Soc. Rev. 1997; 26: 203
7b Kaur M, Choi DH. Chem. Soc. Rev. 2015; 44: 58

8a Walker B, Tamayo AB, Dang X.-D, Zalar P, Seo JH, Garcia A, Tantiwiwat M, Nguyen T.-Q. Adv. Funct. Mater. 2009; 19: 3063
8b Bura T, Leclerc N, Bechara R, Lévêque P, Heiser T, Ziessel R. Adv. Energy Mater. 2013; 3: 1118

9a Li Y, Sonar P, Murphy L, Hong W. Energy Environ. Sci. 2013; 6: 1684
9b Nielsen CB, Turbiez M, McCulloch I. Adv. Mater. 2013; 25: 1859
9c Chandran D, Lee K.-S. Macromol. Res. 2013; 21: 272

10a Fischer GM, Ehlers AP, Zumbusch A, Daltrozzo E. Angew. Chem. Int. Ed. 2004; 126: 10619
10b Fischer GM, Isomäki-Krondahl M, Göttker-Schnetmann I, Daltrozzo E, Zumbusch A. Chem. Eur. J. 2009; 15: 4857

11a Ftouni H, Bolze F, Nicoud J.-F. Dyes Pigm. 2013; 97: 77
11b Ftouni H, Bolze F, de Roquigny H, Nicoud J.-F. Bioconjugate Chem. 2013; 24: 942
11c Zhang G, Li H, Bi S, Song L, Lu Y, Zhang L, Yu J, Wang L. Analyst 2013; 138: 6163
11d Zhang H, Song L, Bi S, Wu Y, Yu J, Yang L. Dyes Pigm. 2014; 102: 100
11e Schmitt J, Heitz V, Sour A, Bolze F, Ftouni H, Nicoud J.-F, Flamigni L, Ventura B. Angew. Chem. Int. Ed. 2015; 54: 169

12a Lin S, Liu S, Ye F, Xu L, Zeng W, Wang L, Li L, Beuerman R, Cao D. Sens. Actuators, B 2013; 182: 176
12b Hang Y, Yang L, Qu Y, Hua J. Tetrahedron Lett. 2014; 55: 6998

13 Shen H, Kou C, He M, Yang H, Liu K. J. Polym. Sci., Part A: Polym. Chem. 2014; 52: 739

For selected recent examples, see:

14a Schmidt CD, Hirsch A In Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry . Pignataro B. Wiley-VCH; Weinheim: 2010: 283
14b Traoré T, Clavé G, Delacour L, Kotera N, Renard P.-Y, Romieu A, Berthault P, Boutin C, Tassali N, Rousseau B. Chem. Commun. 2011; 47: 9702
14c Cole EL, Arunkumar E, Xiao S, Smith BA, Smith BD. Org. Biomol. Chem. 2012; 10: 5769
14d Jiang J, Vairaprakash P, Reddy KR, Sahin T, Pavan MP, Lubian E, Lindsey JS. Org. Biomol. Chem. 2014; 12: 86
14e Thomas AW, Henson ZB, Du J, Vandenberg CA, Bazan GC. J. Am. Chem. Soc. 2014; 136: 3736
14f Wiktorowski S, Rosazza C, Winterhalder MJ, Daltrozzo E, Zumbusch A. Chem. Commun. 2014; 50: 4755
14g Bernhard Y, Winckler P, Chassagnon R, Richard P, Gigot E, Perrier-Cornet J.-M, Decreau RA. Chem. Commun. 2014; 50: 13975

15 Hablot D, Retailleau P, Ziessel R. Chem. Eur. J. 2010; 16: 13346
16 Mula S, Hablot D, Jagtap KK, Heyer E, Ziessel R. New J. Chem. 2013; 37: 303
17 Heyer E, Lory P, Leprince J, Moreau M, Romieu A, Guardigli M, Roda A, Ziessel R. Angew. Chem. Int. Ed. 2015; 54: 2995
18 Huo L, Hou J, Chen H.-Y, Zhang S, Jiang Y, Chen TL, Yang Y. Macromolecules 2009; 42: 6564

19a Kato S.-I, Diederich F. Chem. Commun. 2010; 46: 1994
19b Kato SI, Kivala M, Schweizer W, Boudon C, Gisselbrecht JP, Diederich F. Chem. Eur. J. 2009; 15: 8687
19c Jarowski PD, Wu Y.-L, Boudon C, Gisselbrecht J.-P, Gross M, Schweizer WB, Diederich F. Org. Biomol. Chem. 2009; 7: 1312
19d Reutenauer P, Kivala M, Jarowski PD, Boudon C, Gisselbrecht J.-P, Gross M, Diederich F. Chem. Commun. 2007; 4898

20 Niu S, Ulrich G, Retailleau P, Ziessel R. Tetrahedron Lett. 2011; 52: 4848
21 Esembeson B, Scimeca ML, Michinobu T, Diederich F, Biaggio I. Adv. Mater. 2008; 20: 4584
22 Yamagata T, Kuwabara J, Kanbara T. Eur. J. Org. Chem. 2012; 5282

23a Shoji T, Ito S, Toyota K, Yasunami M, Morita N. Chem. Eur. J. 2008; 14: 8398
23b Shoji T, Higashi J, Ito S, Okujima T, Yasunami M, Morita N. Chem. Eur. J. 2011; 17: 5116
23c Shoji T, Maruyama A, Yaku C, Kamata N, Ito S, Okujima T, Toyota K. Chem. Eur. J. 2015; 21: 402

24a Shoji T, Shimomura E, Maruyama M, Maruyama A, Ito S, Okujima T, Toyota K, Morita N. Eur. J. Org. Chem. 2013; 7785
24b Gautam P, Maragani R, Misra R. Tetrahedron Lett. 2014; 55: 6827
24c Maragani R, Misra R. Tetrahedron 2014; 70: 3390
24d Misra R, Gautam P. Org. Biomol. Chem. 2014; 12: 5448

25 Compound 6: Tetracyanoethylene (41.0 mg, 0.320 mmol, 1.9 equiv) was added to a solution of 5 (144.3 mg, 0.169 mmol) in 1,2-dichloroethane (25 mL). The reaction medium was stirred at 40 °C for 87 h, then evaporated to dryness. Purification by column chromatography (SiO₂, CH₂Cl₂–petroleum ether, 80:20 to 100:0 with 2% Et₃N), followed by recrystallization (THF–n-pentane) afforded 6 (129.6 mg, 78%) as a black powder. ¹H NMR (300 MHz, CDCl₃): δ = 0.83–0.91 (m, 12 H), 1.21–1.40 (m, 16 H), 1.78–1.92 (m, 2 H), 3.84 (s, 6 H), 4.00–4.06 (m, 4 H), 6.81 (d, ³ J = 9.2 Hz, 2 H), 6.92 (d, ³ J = 8.9 Hz, 4 H), 7.16 (d, ³ J = 8.9 Hz, 4 H), 7.33 (dd, ³ J = 5.0, 4.8 Hz, 1 H), 7.67 (d, ³ J = 9.2 Hz, 2 H), 7.77 (dd, ³ J = 5.0 Hz, ⁴ J = 1.0 Hz, 1 H), 7.84 (d, ³ J = 4.5 Hz, 1 H), 9.06 (d, ³ J = 4.5 Hz, 1 H), 9.17 (dd, ³ J = 4.1 Hz, ⁴ J = 0.8 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 10.5, 14.1, 23.2, 23.5, 23.6, 28.3, 28.4, 30.1, 30.2, 39.1, 39.8, 46.2, 46.4, 55.7, 80.1, 108.6, 112.0, 113.0, 113.0, 113.1, 113.9, 115.5, 116.8, 120.0, 125.4, 128.3, 129.1, 129.4, 132.1, 133.3, 135.6, 136.0, 137.1, 137.7, 138.1, 140.2, 144.4, 154.8, 157.5, 158.5, 161.0, 161.9, 162.1. UV/Vis (toluene): λ (ε, M^–1cm^–1) = 691 (37 200), 636 (27 300), 483 (31 500), 333 (16 000) nm. MS (EI): m/z (%) calcd for C₅₈H₅₇N₇O₄S₂: 979.39 (100); found 979.2 (100), 953.2 (25). Anal. Calcd for C₅₈H₅₇N₇O₄S₂ (980.25): C, 71.07; H, 5.86, N, 10.00. Found: C, 70.84; H, 5.47; N, 9.77.
26 Compound 8: Tetracyanoethylene (23.3 mg, 0.182 mmol, 3.4 equiv) was added to a solution of 7 (64.2 mg, 0.054 mmol) in 1,2-dichloroethane (15 mL). The reaction medium was stirred at 40 °C for 18 h, then evaporated to dryness. Purification by column chromatography (Al₂O₃; CH₂Cl₂–petroleum ether, 70:30 to 80:20), followed by recrystallization (THF–n-pentane) afforded 8 (41.6 mg, 54%) as a brownish black powder. ¹H NMR (300 MHz, CDCl₃): δ = 0.83–0.91 (m, 12 H), 1.21–1.36 (m, 16 H), 1.78–1.84 (m, 2 H), 3.82 (s, 12 H), 4.02 (d, ³ J = 7.9 Hz, 4 H), 6.81 (d, ³ J = 9.2 Hz, 4 H), 6.91–6.95 (m, 8 H), 7.13–7.18 (m, 8 H), 7.66 (d, ³ J = 9.4 Hz, 4 H), 7.85 (d, ³ J = 4.6 Hz, 2 H), 9.20 (d, ³ J = 4.6 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 10.4, 14.1, 23.2, 23.4, 28.2, 30.0, 39.7, 46.6, 55.7, 76.5, 81.8, 111.6, 112.7, 112.9, 113.1, 113.8, 115.5, 116.9, 119.8, 128.3, 132.1, 137.1, 137.3, 137.7, 138.8, 139.0, 140.0, 154.9, 157.7, 158.6, 161.1, 161.6. UV/Vis (toluene): λ (ε, M^–1cm^–1) = 749 (48 100), 689 (36 500), 472 (52 700), 393 (27 400) nm. MS (EI): m/z (%) calcd for C₈₆H₇₄N₁₂O₆S₂: 1434.53 (100), 1435.53 (99.3); found: 1435.4 (100), 1408.4 (35), 1382.4 (15). Anal. Calcd for C₈₆H₇₄N₁₂O₆S₂ (1434.71): C, 71.94; H, 5.20, N, 11.71. Found: C, 71.72; H, 4.84; N, 11.49.
27 Compound 14: Tetracyanoethylene (31.0 mg, 0.242 mmol, 2.3 equiv) was added to a solution of 13 (100.4 mg, 0.105 mmol) in 1,2-dichloroethane (25 mL). The round-bottom flask was equipped with a condenser and the mixture was stirred at 50 °C for 48 h. The reaction medium was extracted with CH₂Cl₂, washed with H₂O, and dried with brine and over Na₂SO₄. Purification by column chromatography (SiO₂; petroleum ether–EtOAc, 85:15 to 75:25), followed by precipitation from CH₂Cl₂–MeOH afforded 14 (100.0 mg, 88%) as a black powder. ¹H NMR (400 MHz, CDCl₃): δ = 0.84–0.93 (m, 12 H), 1.21–1.40 (m, 16 H), 1.81–1.87 (m, 1 H), 1.92–1.99 (m, 1 H), 3.82 (s, 6 H), 3.92 (s, 3 H), 4.02–4.08 (m, 4 H), 6.88 (d, ³ J = 8.9 Hz, Dn_{AB syst} = 94.0 Hz, 4 H), 6.91 (d, ³ J = 8.8. Hz, 2 H), 7.05 (d, ³ J = 9.1 Hz, 2 H), 7.11 (d, ³ J = 8.9 Hz, Dn_{AB syst} = 94.0 Hz, 4 H), 7.41 (d, ³ J = 4.4 Hz, 1 H), 7.49 (d, ³ J = 8.8 Hz, 2 H), 7.82 (d, ³ J = 9.1 Hz, 2 H), 7.83 (d, ³ J = 4.7 Hz, 1 H), 9.08 (d, ³ J = 4.6 Hz, 1 H), 9.35 (d, ³ J = 4.3 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 10.52, 10.61, 14.15, 14.21, 23.2, 23.5, 23, 7, 28.3, 28, 5, 30.1, 30.4, 39.3, 39.8, 46.3, 46.5, 55.7, 56.1, 77.9, 78.8, 83.4, 108.5, 111.8, 112.2, 112.5, 113.1, 114.1, 115.0, 115.1, 115.9, 119.3, 123.4, 123.7, 123.9, 126.4, 127.4, 127.5, 127.6, 132.3, 133.8, 135.1, 135.9, 137.8, 139.8, 141.3, 145.0, 150.5, 154.9, 156.0, 156.9, 160.9, 162.3, 165.0, 165.4. UV/Vis (toluene): λ (ε, M^–1cm^–1) = 796 (61 200), 549 (6 300), 372 (39 200) nm. UV/Vis (THF): λ (ε, M^–1cm^–1) = 763 (52 600), 541 (3 400), 370 (38 900) nm. MS (EI): m/z (%) calcd for C₆₅H₆₃N₇O₅S₂: 1085.2 (100), 1086.44 (71); found: 1085.2 (100), 1086.2 (75). Anal. Calcd for C₆₅H₆₃N₇O₅S₂ (1085.43): C, 71.86; H, 5.85, N, 9.03. Found: C, 71.60; H, 5.69; N, 8.77.
28 Iqbal A, Jost M, Kirchmayr R, Pfenninger J, Rochat A, Wallquist O. Bull. Soc. Chim. Belg. 1988; 97: 615
29 Hablot D, Harriman A, Ziessel R. Angew. Chem. Int. Ed. 2011; 50: 7833
30 Lakowicz JR. In Principles of Fluorescence Spectroscopy 2006
31 Niu S, Ulrich G, Retailleau P, Ziessel R. Org. Lett. 2011; 13: 4996
32 Jayamurugan G, Gisselbrecht J.-P, Boudon C, Schoenebeck F, Schweizer WB, Bernet B, Diederich F. Chem. Commun. 2011; 47: 4520
33 These values were calculated by using the E ₀₀ values of dyes 5 and 7 obtained by using the intersection between the absorption and emission at respectively 623 and 655 nm and the shift in absorption of dyes 6 and 8 with respect to the corresponding dyes 5 and 7.

34a Rehm D, Weller A. Ber. Bunsen-Ges. 1969; 73: 834
34b Rehm D, Weller A. Isr. J. Chem. 1970; 259

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