Crystal growth and characterization of fluorinated perylene diimides

Abstract

One-dimensional crystals of fluorinated perylene diimides were achieved by the self-assembly of them via solvent-nonsolvent exchanging. The π-conjugated fluorinated perylene diimides were assembled into highly-ordered nanostructures of well-defined morphologies in organic solvents due to the π-π interaction between the aromatic cores. It was found that with more introduced F atoms, perylene diimides showed remarkably improved solubility and thus were much easier to grow into crystals, due to the increased polarity induced by the strong electron-withdrawing F group. More importantly, single crystal of N,N′-diperfluorophenyl-3,4,9,10-perylenetetracarboxylic diimide(DPFPP) was obtained, and the unit cell-dimensions of triclinic structure were determined by the selected area electron diffraction( SAED) patterns to be a=0.712 nm, b=1.072 nm, c=2.914 nm, α=97.0°, β=89.6°, γ=93.4°. Owing to most of the longest c-axis orienting nearly vertically to the long axis of the needle crystal, the molecular planes are expected to be vertical to the needle axis.

Keywords

Perylene diimide / Fluorination / Crystal growth

References

[1] Sekitani T, Nakajima H, Maeda H, Fukushima T, Aida T, Hata K, Someya T. Nat. Mater., 2009, 8: 494.

[2] Gelinck G H, Huitema H E A, Veenendaal E, Cantatore E, Schrijnemakers L, Putten J B P H, Geuns T C T, Beenhakkers M, Giesbers J B, Huisman B H, Meijer E J, Benito E M, Touwslager F J, Marsman A W, Rens B J E, Leeuw D M. Nat. Mater., 2004, 3: 106.

[3] Sekitani T, Yokota T, Zschieschang U, Klauk H, Bauer S, Takeuchi K, Takamiya M, Sakurai T, Someya T. Science, 2009, 326: 1516.

[4] Sokolov A N, Roberts M E, Johnson O B, Cao Y, Bao Z. Adv. Mater., 2010, 22: 2349.

[5] Spijkman M J, Brondijk J J, Geuns T C T, Smits E C P, Cramer T, Zerbetto F, Stoliar P, Biscarini F, Blom P W M, Leeuw D M. Adv. Funct. Mater., 2010, 20: 898.

[6] Qu Y, Hua J, Tian H. Org. Lett., 2010, 12: 3320.

[7] Yamagata T, Kuwabara J, Kanbara T. Tetrahedron Lett., 2010, 51: 1596.

[8] Deng L, Wu W, Guo H, Zhao J, Ji S, Zhang X, Yuan X, Zhang C. J. Org. Chem., 2011, 76: 9294.

[9] You J, Dou L, Yoshimura K, Liu Q S, Zhu G S, Sun F X. Nat. Commun., 2013, 4: 1446.

[10] Li Y F. Acc. Chem. Res., 2012, 45(5): 723.

[11] Lin Y, Li Y F, Zhan X W. Chem. Soc. Rev., 2012, 41: 4245.

[12] Sun Y, Welch G C, Leong W L, Takacs C J, Bazan G C, Heeger A J. Nat. Mater., 2012, 11: 44.

[13] He Z, Zhong C, Su S, Xu M, Wu H, Cao Y. Nature Photonics, 2012, 6: 591.

[14] Sonar P, Ng G M, Lin T T, Dodabalapur A, Chen Z K. Mater. Chem., 2010, 20: 3626.

[15] Karsten B P, Bijleveld J C, Janssen R A J. Macromol. Rapid Commun., 2010, 31: 1554.

[16] Lin Y, Cheng P, Li Y, Zhan X. Chem. Commun., 2012, 48: 4773.

[17] Walker B, Kim C, Nguyen T Q. Chem. Mater., 2011, 23: 470.

[18] Hu X L, Shi M M, Zuo L J, Fu L, Dai S L, Chen H Z. Acta Chim. Sin., 2011, 69: 673.

[19] Li B. Chem. J. Chinese Universities, 2013, 34(2): 429.

[20] Li H Y, Tee B C K, Giri G, Chung J W, Lee S Y, Bao Z. Adv. Mater., 2012, 24: 2588.

[21] Sundar V C, Zaumseil J, Podzorov V, Menard E, Willett R L, Someya T, Gershenson M E, Rogers J A. Science, 2004, 303: 1644.

[22] Sirringhaus H. Adv. Mater., 2005, 17: 2411.

[23] Wang C L, Dong H L, Hu W P, Liu Y Q, Zhu D B. Chem. Rev., 2012, 112: 2208.

[24] Allard S, Forster M, Souharce B, Thiem H, Scherf U. Angew. Chem. Int. Ed., 2008, 47: 4070.

[25] Du S S, Zhao C B, Ma Y, Wang W L. Chem. J. Chinese Universities, 2013, 34(1): 161.

[26] Zang L, Che Y, Moore J S. Acc. Chem. Res., 2008, 41: 1596.

[27] Li W S, Saeki A, Yamamoto Y, Fukushima T, Seki S, Ishii N, Kato K, Takata M, Aida T. Chem. Asian J., 2010, 5: 1566.

[28] Li R, Hu W, Liu Y, Zhu D. Acc. Chem. Res., 2010, 43: 529.

[29] Li Z, Xu F. Chin. J. Chem., 2005, 23: 337.

[30] Li H Y, Giri G, Tok J B H, Bao Z. MRS Bull., 2013, 38: 34.

[31] Li H Y, Tee B C K, Cha J J, Cui Y, Chung J W, Lee S Y, Bao Z. J. Am. Chem. Soc., 2012, 134: 2760.

[32] Akkerman H B, Chang A C, Verploegen E, Bettinger C J, Toney M F, Bao Z. Organic Electronics, 2012, 13: 235.

[33] Podzorov V, Menard E, Borissov A, Kiryukhin V, Rogers J A, Gershenson M E. Phys. Rev. Lett., 2004, 93: 086602.

[34] Jurchescu O D, Baas J, Palstra T T. Appl. Phys. Lett., 2004, 84: 3061.

[35] Hasegawa T, Takeya J. Sci. Technol. Adv. Mater., 2009, 10: 024314.

[36] Pfattner R, Mas-Torrent M, Bilotti I, Brillante A, Milita S, Liscio F, Biscarini F, Marszalek T, Ulanski J, Nosal A, Gazicki-Lipman M, Leufgen M, Schmidt G, Molenkamp L W, Laukhin V, Veciana J, Rovira C. Adv. Mater., 2010, 22: 4198.

[37] Wen Y, Liu Y. Adv. Mater., 2010, 22: 1331.

[38] Anthony J E, Facchetti A, Heeney M, Marder S R, Zhan X. Adv. Mater., 2010, 22: 3876.

[39] Che Y, Datar A, Balakrishnan K, Zang L. J. Am. Chem. Soc., 2007, 129: 7234.

[40] Balakrishnan K, Datar A, Naddo T, Huang J, Oitker R, Yen M, Zhao J, Zang L. J. Am. Chem. Soc., 2006, 128: 7390.

[41] Balakrishnan K, Datar A, Oitker R, Chen H, Zuo J M, Zang L. J. Am. Chem. Soc., 2005, 127: 10496.

[42] Wurthner F. Chem. Commun., 2004, 14: 1564.

[43] Newman C R, Frisbie C D, da Silva D A, Bredas J L, Ewbank P C, Mann K R. Chem. Mater., 2004, 16: 4436.

[44] Oh J H, Lee H W, Mannsfeld S, Stoltenberg R M, Jung E, Jin Y W, Kim J M, Yoo J B, Bao Z. PNAS, 2009, 106(15): 6065.

[45] Chen H Z, Ling M M, Mo X, Shi M M, Wang M, Bao Z. Chem. Mater., 2007, 19: 816.

[46] Shi M M, Chen H Z, Wang M. Acta Chim. Sin., 2006, 64: 721.

[47] Huang J C, Yang L G, Mo X, Shi M M, Wang M, Chen H Z. Acta Chim. Sin., 2007, 65: 1051.

[48] Shi M M, Chen H Z, Sun J Z, Ye J, Wang M. Chem. Commun., 2003, 14: 1710.

[49] Katz H E, Johnson J, Lovinge A J, Li W. J. Am. Chem. Soc., 2000, 122: 7787.

[50] Katz H E, Lovinger A J, Johnson J, Kloc C, Siegrist T, Li W, Lin Y Y, Dodabalapur A. Nature, 2000, 404: 478.

[51] Che Y, Yang X, Loser S, Zang L. Nano Lett., 2008, 8(8): 2219.