1. bookVolume 36 (2018): Issue 2 (June 2018)
Journal Details
License
Format
Journal
eISSN
2083-134X
First Published
16 Apr 2011
Publication timeframe
4 times per year
Languages
English
access type Open Access

Quinoxaline-Based Small Molecules: Synthesis and Investigation on Their Optoelectronic Properties

Published Online: 25 Jun 2018
Volume & Issue: Volume 36 (2018) - Issue 2 (June 2018)
Page range: 167 - 176
Received: 27 Jul 2017
Accepted: 11 Feb 2018
Journal Details
License
Format
Journal
eISSN
2083-134X
First Published
16 Apr 2011
Publication timeframe
4 times per year
Languages
English
Abstract

Small molecules of ThQuTh, CzQuTh, CzQuCz and TPAQuCz were designed and synthesized, based on quinoxaline acceptor, and electron donating groups, i.e. alkyl-thioephene, carbazole and triphenylamine on both side chains and molecular backbones. Their thermal, optical and electrochemical properties were systematically compared and studied. The absorption spectra of the small molecules were strongly affected by the donor units attached to quinoxaline. Strong electron donating groups, such as carbazole on the molecular backbone would lower optical band gap, resulting in a wide absorption and the strong donor on the side chain would enhance the absorption intensity in short wavelength region. The highest occupied molecular orbital (HOMO) energy levels of the four molecules were up-shifted with increasing the electron donating properties of donor units. The bulk-heterojunction organic solar cells with a device structure of ITO/PEDOT:PSS/SMs:PC61BM/LiF/Al were fabricated, in which the small molecules functioned as donors while PC61BM as acceptor. Because the electron-donating ability of carbazole (Cz), triphenylamine (TPA) is higher than that of thiophene (Th), CzQuTh, CzQuCz and TPAQuCz show higher power conversion efficiency (PCE) than that of ThQuTh. Furthermore, being the strongest in absorption intensity and widest in absorption spectrum, TPAQuCz has the highest power conversion efficiency. Further improvement of the device efficiency by optimizing the device structure is currently under investigation

Keywords

[1] Jin Y., Chen Z., Dong S., Zheng N., Ying L., Jiang X.F., Liu F., Huang F., Cao Y., Adv. Mater., 28 (2016), 9811.Search in Google Scholar

[2] Lee J., Sin D.H., Moon B., Shin J., Kim H.G., Kim M., Cho K., Energ. Environ. Sci., 10 (2017), 24710.1039/C6EE02466ASearch in Google Scholar

[3] Ro H.W., Downing J.M., Engmann S., Herzing A.A., Delongchamp D.M., Richter L.J., Mukherjee S., Ade H., Abdelsamie M., Jagadamma L.K., Amassian A., Liu Y., Yan H., Solar Cell. Energy Environ. Sci., 9 (2016), 283510.1039/C6EE01623EOpen DOISearch in Google Scholar

[4] Zhang B., Liang J.F., Hu L.W., Peng F., Chen G.T., Yang W., J Mater Sci., 16 (2015), 5609.10.1007/s10853-015-9111-0Search in Google Scholar

[5] Liu Y., Zhao J., Li Z., Mu C., Ma W., Hu H., Jiang K., Lin H., Ade H., Yan H., Nat. Commun., 5 (2014), 5293.10.1038/ncomms6293424243625382026Search in Google Scholar

[6] Li Y., Yue G.T., Chen X.X., He B.L., Chu L., Chen H.Y., Wu J.H., Tang Q.W., J Mater Sci., 9 (2013), 3528.10.1007/s10853-013-7147-6Open DOISearch in Google Scholar

[7] Zheng Z., Zhang S., Zhang J., Qin Y., Li W., Yu R., Wei Z., Hou J., Adv. Mater., 28 (2016), 5133.10.1002/adma.20160037327136384Open DOISearch in Google Scholar

[8] Qiao F., Liu A.M., Hu Z.Q., Liu Y.T., Yu S.W., Zhou Z.G., J. Mater. Sci., 13 (2009), 3462.10.1007/s10853-009-3461-4Search in Google Scholar

[9] Zhao J., Li Y., Yang G., Jiang K., Lin H., Ade H., Ma W., Yan H., Nat. Energy, 1 (2016), 15027.10.1038/nenergy.2015.27Search in Google Scholar

[10] Zhao G.J., Wu G.L., He C., Bai F.Q., Xi H.X., Zhang H.X., Li Y.F., J. Phys. Chem., 113 (2009), 2636.10.1021/jp809795pSearch in Google Scholar

[11] Wu G., Zhao G., He C., Zhang J., He Q., Chen X., Li Y., Sol. Energ. Mater. Sol. C., 93 (2009), 108.10.1016/j.solmat.2008.09.001Open DOISearch in Google Scholar

[12] Lin Y., Li Y., Zhan X., Chem. Soc. Rev., 41 (2012), 4245.10.1039/c2cs15313k22453295Open DOISearch in Google Scholar

[13] Mishra A., Bauerle P., Ang. Chem., 51 (2012), 2020.10.1002/anie.20110232622344682Search in Google Scholar

[14] Coughlin J., Henson Z., Welch G., Bazan G., Chem. Res., 47 (2014), 257.10.1021/ar400136b23984626Open DOISearch in Google Scholar

[15] Chen Y., Wang X., Long G., Acc. Chem. Res., 46 (2013), 2645.10.1021/ar400088c23902284Open DOISearch in Google Scholar

[16] Wang D., Ding W., Geng Z., Wang L., Geng Y., Su Z., Yu H., Mater. Chem. Phys., 145 (2014), 387.10.1016/j.matchemphys.2014.02.027Search in Google Scholar

[17] Kan B., Li M., Zhang Q., Liu F., Wan X., Wang Y., Ni W., Long G., Yang X., Feng H., Zuo Y., Zhang M., Huang F., Cao Y., Russell T.P., Chen Y.A., J. Am. Chem. Soc., 137 (2015), 3886.10.1021/jacs.5b0030525736989Search in Google Scholar

[18] Shi Q., Cheng P., Li Y., Zhan X., Adv. Energ. Mater., 2(2012), 63.10.1002/aenm.201100505Search in Google Scholar

[19] Lincker F., Delbosc N., Bailly S., De Bettignies R., Billon M., Pron A., Demadrille R., Adv. Funct. Mater., 18 (2008), 3444.10.1002/adfm.200800366Open DOISearch in Google Scholar

[20] Zhang J., Yang Y., He C., He Y., Zhao G., Li Y., Macromolecules, 42 (2009), 7619.10.1021/ma901896nOpen DOISearch in Google Scholar

[21] Yang Y., Zhang J., Zhou Y., Zhao G., He C., Li Y., Andersson M., Inganas O., Zhang F., J. Phys. Chem. C, 114 (2010), 3701.10.1021/jp910836tSearch in Google Scholar

[22] Zheng Z., Awartani O.M., Gautam B., Liu D., Qin Y., Li W., Bataller A., Gundogdu K., Ade H., Hou J., Adv. Mater., 5 (2016), 29.10.1002/adma.20160424127893177Search in Google Scholar

[23] Fan Q., Xiao M., Liu Y., Su W., Gao H., Tan H., Wang Y., Lei G., Yang R., Zhu W., Polym. Chem., 6 (2015), 4290.10.1039/C5PY00305ASearch in Google Scholar

[24] Su W., Xiao M., Fan Q., Zhong J., Chen J., Dang D., Shi J., Xiong W., Duan X., Tan H., Liu Y., Zhu W., Org. Electron., 17 (2015), 129.Search in Google Scholar

[25] Fan Q., Liu Y., Xiao M., Su W., Gao H., Chen J., Tan H., Wang Y., Yang R., Zhu W., J. Mater. Chem. C, 3 (2015), 6240.Search in Google Scholar

[26] Lee D.-C., Brownell V.L., Yan L., You W., Acs Appl. Mater. Interfaces, 6 (2014), 15767.10.1021/am502753825166930Open DOISearch in Google Scholar

[27] Chang D. W., Ko S.-J., Kim J.Y., Dai L., Baek J.-B., Synth. Met., 162 (2012), 1169.10.1016/j.synthmet.2012.04.016Search in Google Scholar

[28] Li W., Wang D., Wang S., Ma W., Hedstroem S., James D. I., Xu X., Persson P., Fabiano S., Berggren M., Inganaes O., Huang F., Wang E., Acs Appl. Mater. Inter., 7 (2015), 27106.10.1021/acsami.5b0946026592898Search in Google Scholar

[29] Velusamy M., Huang J.H., Hsu Y.C., Chou H.H., Ho K.C., Wu P.L., Chang W.H., Lin J.T., Chu C.W., Org. Lett., 11 (2009), 4989.10.1021/ol901995319780591Search in Google Scholar

[30] Hagemann O., Jørgensen M., Krebs F.C., J. Org. Chem., 71 (2006), 5546.10.1021/jo060491r16839133Search in Google Scholar

[31] Lim B., Baeg K.J., Jeong H.G., Jo J., Kim H., Park J.W., Noh Y.Y., Vak D., Park J.H., Park J.W., Kim D.Y., Adv. Mater., 21 (2009), 2808.10.1002/adma.200803700Search in Google Scholar

[32] Svensson M., Zhang F., Veenstra S.C., Verhees W.J.H., Hummelen J.C., Kroon J.M., Inganas O., Adv. Mater., 15 (2003), 988.10.1002/adma.200304150Search in Google Scholar

[33] Xu M.F., Li R.Z., Pootrakulchote N., Shi D., Guo J., Yi Z.H., Zakeeruddin S.M., Gratzel M., Wang P., J. Phys. Chem., 112 (2008), 19770. B) Liu M., Wang Y.F., Zhang Z.Y., Li J.M., Liu Y., Tan H., Ni M.J., Lei G.T., Zhu M.X., Zhu W.G., J. Polym. Sci. Pol. Chem., 49 (2011), 3874.Search in Google Scholar

[34] Li Z., Dong Q., Xu B., Li H., Wen S., Pei J., Yao S., Lu H., Li P., Tian W., Sol. Energ. Mater. Sol. C., 95 (2011), 2272.10.1016/j.solmat.2011.03.040Search in Google Scholar

[35] Zhang W.F., Ng G.M., Tam H.L., Wong M.S., Zhu F.S., J. Poly. Sci. Part A: Poly. Chem., 49 (2011), 1865.10.1002/pola.24613Search in Google Scholar

[36] So S., Choi H., Kim C., Cho N., Ko H.M., Lee J.K., Ko J., Sol. Energ. Mater. Sol. C, 95 (2011), 3433.10.1016/j.solmat.2011.07.034Search in Google Scholar

[37] Li Y.F., Cao Y., Gao J., Wang D.L., Yu G., Heeger A.J., Synth. Met., 99 (1999), 243.10.1016/S0379-6779(99)00007-7Search in Google Scholar

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