全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
化学进展  2015 

齐聚噻吩及其衍生物有机光伏材料

DOI: 10.7536/PC150328, PP. 1435-1447

Keywords: 齐聚噻吩,光伏性能,有机光伏器件,有机太阳能电池

Full-Text   Cite this paper   Add to My Lib

Abstract:

齐聚噻吩及其衍生物具有良好的环境稳定性和优异的光电性能,是一类具有良好发展前景的有机功能材料。本文综述了近年来齐聚噻吩及其衍生物的发展状况,简述了其主要合成方法;根据结构将其分为两大类一类是不含极性基团或仅含弱极性基团的齐聚噻吩衍生物,另一类是给体-受体型齐聚噻吩衍生物,并讨论了它们作为有机光伏材料的应用。给体-受体型齐聚噻吩衍生物由于分子内的电荷传输作用,其光物理和电化学性能均优于不含极性基团的齐聚噻吩,该类材料在小分子光伏器件中具有最高的光电转换效率(>10%)。文章最后简要分析了影响光伏器件性能的主要因素。

References

[1]  Liu Q, Zhan H, Ho C L, Dai F R, Fu Y, Xie Z, Wang L, Li J H, Yan F, Huang S P, Wong W Y. Chemistry-an Asian Journal, 2013, 8(8): 1892.
[2]  Montcada N F, Pelado B, Viterisi A, Albero J, Coro J, de la Cruz P, Langa F, Palomares E. Organic Electronics, 2013, 14(11): 2826.
[3]  Li P C, Tong H, Ding J Q, Xie Z Y, Wang L X. J. Mater. Chem. A: Materials for Energy and Sustainability, 2013, 1(31): 8805.
[4]  Nakanishi H, Sumi N, Aso Y, Otsubo T. J. Org. Chem., 1998, 63: 8632.
[5]  Albers W M. Tetrahedron, 1995, 51(13): 3895.
[6]  Kosugi M, Shimizu Y, Migita T. Chem. Lett., 1977, 12: 1423.
[7]  Milstein D, Stille J K. J. Am. Chem. Soc., 1978, 100: 3636.
[8]  Stille J K. Angew. Chem., Int. Ed., 1986, 25: 508.
[9]  Osun R M, Ortiz R P, Ruiz Delgado M C, Sakamoto Y, Suzuki T, Hernandez V, López Navarrete J T. J. Phys. Chem. B, 2005, 109: 20737.
[10]  Ie Y, Umemoto Y, Okabe M, Kusunoki T, Nakayama K I, Pu Y J, Kido J, Tada H, Aso Y. Org. Lett., 2008, 10(5): 833.
[11]  Henssler J T, Zhang X N, Matzger A J. J. Org. Chem., 2009, 74: 9112.
[12]  Li Y, Hong X M, Collard D M, El-Sayed M A. Org. Lett., 2000, 2(15): 2385.
[13]  Melucci M, Barbarella G, Zambianchi M, Di Pietro P, Bongini A. J. Org. Chem., 2004, 69: 4821.
[14]  ?slund A, Sigurdson C J, Klingstedt T, Grathwohl S, Bolmont T, Dickstein D L, Glimsdal E, Prokop S, Lindgren M, Konradsson P, Holtzman D M, Hof P R, Heppner F L, Gandy S, Jucker M, Aguzzi A, Hammarstr?m P, Nilsson K P. ACS Chem. Bio., 2009, 4(8): 673.
[15]  Hanène Bedis, Fay?al Kouki, Habib Bouchriha. Appl. Phys. A, 2013, 110: 163.
[16]  Niu Q F, Lu Y Q, Sun H J, Li X Y, Tao X T. Dyes and Pigments, 2013, 97: 184.
[17]  Kwon J, Hong J P, Noh S, Kim T M, Kim J J, Lee C, Lee S, Hong J I. New J. Chem., 2012, 36: 1813.
[18]  Gebeyehu D, Maening B, Drechsel J, Leo K, Pfeiffer M, Sol. Energy Mater. Sol. Cells, 2003, 79: 81.
[19]  Azumi R, Goto M, Honda K, Matsumoto M. Bull. Chem. Soc. Jpn., 2003, 76: 1561.
[20]  Shibata Y, Kono T, Komura Ni, Yoshida Y. Organic Electronics, 2013, 14: 1073.
[21]  Pappenfus T M, Mann K R. Org. lett., 2002, 4(18): 3043.
[22]  Shang H X, Fan H J, Liu Y, Hu W P, Li Y F, Zhan X W. J. Mater. Chem., 2011, 21: 9667.
[23]  Wright I A, Findlay N J, Arumugam S, Inigo A R, Kanibolotsky A L, Zassowski P, Domagala W, Skabara P J. J. Mater. Chem. C, 2014, 2: 2674.
[24]  Roquet S, Cravino A, Leriche P, Alévêque O, Frère P, Roncali J. J. Am. Chem. Soc., 2006, 128: 3459.
[25]  Bader M M, Pham P T, Elandaloussi E H. Crystal Growth & Design, 2010, 10(12): 5027.
[26]  Li Z, Dong Q, Li Y, Xu B, Deng M, Pei J, Zhang J, Chen F, Wen S, Gao Y, Tian W. J. Mater. Chem., 2011, 21: 2159.
[27]  Lincker F, Delbosc N, Bailly S, De Bettigines R, Billon M, Pron A, Demadrille R. Adv. Funct. Mater., 2008, 18: 3444.
[28]  Mayerh?ffer U, Deing K, Gruss K, Braunschweig H, Meerholz K, Würthner F. Angew. Chem., Int. Ed., 2009, 48: 8776.
[29]  Walker B, Tamayo A B, Dang X D, Zalar P, Seo J H, Garcia A, Tantiwiwat M, Nguyen T Q. Adv. Funct. Mater., 2009, 19: 3063.
[30]  Mei J, Graham K R, Stalder R, Reynolds J R. Org. Lett. 2010, 12: 660.
[31]  Steinberger S, Mishra A, Reinold E, Müller C M, Uhrich C, Pfeiffer M, B?uerle P. Org. Lett., 2011, 13: 90.
[32]  Schulze K, Uhrich C, Schüppel R, Leo K, Pfeiffer M. Adv. Mater., 2006, 18: 2872.
[33]  Uhrich C, Schueppel R, Petrich A, Pfeiffer M, Leo K, Brier E, Kilickiran P, B?uerle P. Adv. Funct. Mater., 2007, 17: 2991.
[34]  Haid S, Mishra A, Uhrich C, Pfeiffer M, B?uerle P. Chem. Mater., 2011, 23: 4435.
[35]  Fitzner R, Reinold E, Mishra A, Mena-Osteritz E, Ziehlke H, K?rner C, Leo K, Riede M, Weil M, Tsaryova O, WeiB A, Uhrich C, Pfeiffer M, B?uerle P. Adv. Funct. Mater., 2011, 21: 897.
[36]  Steinberger S, Mishra A, Reinold E, Levichkov J, Uhrich C, Pfeiffer M, B?uerle P. Chem. Commun., 2011, 47: 1982.
[37]  Cui C H, Min J, Ho C L, Ameribc T, Yang P, Zhao J Z, Brabec C J, Wong W Y. Chem. Commun., 2013, 49: 4409.
[38]  He G R, Li Z, Wan X J, Liu Y S, Zhou J Y, Long G K, Zhang M T, Chen Y S. J. Mater. Chem., 2012, 22: 9173.
[39]  He G, Li Z, Wan X, Zhou J, Long G, Zhang S, Zhang M, Chen Y. J. Mater. Chem. A, 2013, 1, 1801.
[40]  Liu Y S, Wan X J, Wang F, Zhou J Y, Long G K, Tian J G, Chen Y S. Adv. Mater., 2011, 23, 5387.
[41]  Lin Y Z, Ma L C, Li Y F, Liu Y Q, Zhu D B, Zhan X W, Advanced Energy Materials, 2014, 4(1), 1300626/1.
[42]  Chen Y J, Li C, Zhang P, Li Y W, Yang X M, Chen L W, Tu Y F. Organic Electronics, 2013, 14: 1424.
[43]  Hu J H, Liang L S, Chen T H, Liu P, Deng W J. Dyes and Pigments, 2014, 100: 158.
[44]  Arnold B, Walker B, Nguyen T Q. Journal of Physics Chemistry C, 2008, 112: 11545.
[45]  Li Z F, Dong Q Fg, Xu B, Cheng W D, Yao S Y, Zhang X Y, Wen S P, Li H, Dong Y J, Tian W J. Solar Energy Materials & Solar Cells, 2012, 98: 343.
[46]  Leliège A, Blanchard P, Rousseau T, Roncali J. Org. Lett., 2011, 13(12): 3098..
[47]  Xia P F, Feng X J, Lu J P, Movileanu R, Tao Y, Baribeau J M, Wong M S. J. Phys. Chem. C, 2008, 112: 16714.
[48]  Steinberger S, Mishra A, Reinold E, Mena-Osteritz E, Müller H, Uhrich C, Pfeiffer M, B?uerle P. J. Mater. Chem., 2012, 22: 2701.
[49]  Sun Y M, Welch G C, Leong W L, Takacs C J, Bazan G C, Heeger A J. Nature Materials, 2012, 11: 44.
[50]  Luponosov Y N, Min J, Ameri T, Brabec C J, Ponomarenko S A. Organic Electronics, 2014, 15(12): 3800.
[51]  Mishra A, Popovic D, Vogt A, Kast H, Leitner T, Walzer K, Pfeiffer M, Mena-Osteritz E, B?uerle P. Advan. Mater., 2014, 26(42): 7217.
[52]  Li Z F; Bian J, Wang Y I, Jiang F Y, Liang G J, He P, Hou Q F, Tong J H, Liang Y, Zhong Z C. Solar Energy Materials & Solar Cells, 2014, 130: 336.
[53]  Weidelener M, Wessendorf C D, Hanisch J, Ahlswede E, G?tz G, Linde M, Schulz G, Mena-Osteritz E, Mishra A, B?uerle P. Chemical Communications, 2013, 49(92): 10865.
[54]  Zerdan R B, Shewmon N T, Zhu Y, Mudrick J P, Chesney K J, Xue J G, Castellano R K. Adv. Funct. Mater., 2014, 24(38): 5993.
[55]  Wessendorf C D, Schulz G L, Mishra A, Kar P, Ata I, Weidelener M, Urdanpilleta M, Hanisch J, Mena-Osteritz E, Lindén M, Ahlswede E, B?uerle P. Adv. Energy Mater., 2014, 4: 1400266.
[56]  Kan B, Zhang Q, Li M, Wan X, Ni W, Long G, Wang Y, Yang X, Feng H, Chen Y. J. Am. Chem. Soc., 2014, 136: 15529.
[57]  Zhang Q, Kan B, Liu F, Long G, Wan X, Chen X, Zuo Y, Ni W, Zhang H, Li M, Hu Z, Huang F, Cao Y, Liang Z, Zhang M, Russell T P, Chen Y. Nat. Photonics, 2015, 9: 35.
[58]  Zuo Y, Zhang Q, Wan X, Li M, Zhang H, Li C, Chen Y. Organic Electronics, 2015, 19: 98.
[59]  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. J. Am. Chem. Soc, DOI: 10.1021/jacs.5b00305
[60]  Rance W L, Rupert B L, Mitchell W J, K?se M E, Ginley D S, Shaheen S E., Rumbles G, Nikos K. J. Phys. Chem. C, 2010, 114: 22269.
[61]  Zhang W F, Meng G NG, Tam H L, Wong M S, Zhu F R. J. Poly. Sci. Part A: Polymer Chemistry, 2011, 49: 1865.
[62]  Lincker F, Heinrich B Bettignies R D, Rannou P, Pécaut J, Grévin B, Pron A, Donnio B, Demadrille R. J. Mater. Chem., 2011, 21: 5238.
[63]  Kylberg W, Zhang Y, Aebersold A, Castro F A d, Geiger T, Heier J, Kuster S, Ma C Q, B?uerle P, Nüesch F, Tisserant J N, Hany R. Organic Electronics, 2012, 13: 1204.
[64]  Zhang J, Deng D, He C, He Y J, Zhang M J, Zhang Z G, Zhang Z J, Li Y F. Chem. Mater. 2011, 23: 817.
[65]  Lin Y Z, Zhang Z G, Bai H T, Li Y F, Zhan X W. Chem. Commun., 2012, 48: 9655.
[66]  Shang H X, Fan H J, Liu Y, Hu W P, Li Y F, Zhan X W. Adv. Mater., 2011, 23: 1554.
[67]  Shen S L, G L, He C, Zhang Z J, Sun Q J, Li Y F. Organic Electronics, 2013, 14(3): 875.
[68]  Min J, Luponosov Y N, Baran D, Chvalun S N, Shcherbina M A, Bakirov A V, Dmitryakov P V, Peregudova S M, Kausch-Busies N, Ponomarenko S A, Ameri T, Brabec C J. J. Mater. Chem. A, 2014, 2(38): 16135.
[69]  Wong W W H, Ma C Q, Pisula W, Mavrinskiy A, Feng X L, Seyler H, Jones D J, Müllen K, B?uerle P, Holmes A B. Chem. Eur. J., 2011, 17: 5549.
[70]  Takemoto K, Karasawa M, Kimura M. ACS Appl. Mater. Interfaces, 2012, 4: 6289.
[71]  Mei J G, Graham K R, Stalder R, Tiwari S P, Cheun H, Shim J, Yoshio M, Nuckolls C, Kippelen B, Castellano R K, Reynolds J R. Chem. Mater., 2011, 23: 2285.
[72]  Siram R B K, Tandy K, Horecha M, Formanek P, Stamm M, Gevorgyan S, Krebs F C, Kiriy A, Meredith P, Burn P L, Namdas E B, Patil S. J. Phys. Chem. C, 2011, 115: 14369.
[73]  Izawa S, Hashimoto K, Tajima K. Syn. Meta., 2012, 162: 2201.
[74]  Chen T L, Zhang Y, Smith P, Tamayo A, Liu Y, Ma B. ACS Appl. Mater. Interfaces, 2011, 3: 2275.
[75]  Nicolaidis N C, Routley B S, Holdsworth J L, Belcher W J, Zhou X, Dastoor P C, J. Phys. Chem. C, 2011, 115: 7801.
[76]  Arbogast J W, Foote C S. J. Am. Chem. Soc., 1991, 113: 8886.
[77]  Xiao Z, Ye G, Liu Y, Chen S, Peng Q, Zuo Q Q, Ding L M. Angew. Chem. Int. Ed., 2012, 51: 9038.
[78]  Wang C G, Chen W P, Chen S Y, Zhao S S, Zhang J Y, Qiu D L, Wang Y. New J. Chem., 2012, 36: 1788.
[79]  Ahmed E , Ren G, Kim F S, Hollenbeck E C, Jenekhe S A. Chem. Mater., 2011, 23: 4563.
[80]  Aoyagi K, Shoji Y, Otsubo S, Kawauchi S, Ueda M, Matsumoto H, Higashihara T. Bulletin of the Chemical Society of Japan, 2014, 87(10): 1083.
[81]  Ni W, Li M, Kan B, Zuo Y, Zhang Q, Long G, Feng H, Wan X, Chen Y. Organic Electronics, 2014, 15: 2285.
[82]  Li Z F, Pei J N, Li Y W, Xu B, Deng M, Liu Z Y, Li H, Lu H G, Li Q, Tian W J. J. Phys. Chem. C, 2010, 114: 18270.
[83]  Zhao G J, He Y J, He C, Fan H J, Zhao Y, LiY F. Solar Energy Materials & Solar Cells, 2011, 95: 704.
[84]  Gupta A, Ali A, Bilic A, Gao M, Hegedus K, Singh B, Watkins S E, Wilson G J, Bach U, Evans R A. Chem. Commun., 2012, 48: 1889.
[85]  Sasaki K, Shibata Y, Lu M, Yoshida Y, Azumi R, Ueda Y. Advances in Materials Physics and Chemistry, 2013, 3(2): 185.
[86]  Kwok E C H, Tsang D P K, Chan M Y, Yam V W W. Chem. Eur. J., 2013, 19: 2757.
[87]  Spiekermann S, Smestad G. Synthetic Metals, 2001, 121: 1603.
[88]  Zhang S Q, Ye L, Zhao W C, Yang B, Wang Q, Hou J H. Science China Chemistry, 2015, 58(2): 248.
[89]  Pei J, Yu W L, Heeger A J, Huang W. Macromolecules, 2000, 33(7): 2462.
[90]  Roncali J. Chemical Review, 1992, 92(4): 711.
[91]  Ma W, Yong C, Gong X, Lee K, Heeger A J. Adv. Funct. Mater., 2005, 15(10): 1617.
[92]  Ayzner A L, Wanger D D, Tassone C J, Tolbert S H, Schwartz B J. J. Phys. Chem. C, 2008, 112: 18711.
[93]  Chu C W, Yang H, Hou W J, Huang J S, Li G, Yang Y. Appl. Phys. Lett., 2008, 92: 103306.
[94]  Richard D, Cullough M. Adv. Funct. Mater., 1998, 10(2): 93.
[95]  Armstrong N R, Carter C. Thin Solid Films, 2003, 445: 343.
[96]  Kim K, Liu J, Namboothiry M A G, Carroll D L. Appl. Phys. Lett., 2007, 90: 163511.
[97]  Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc., 1972, 94: 4374.
[98]  Zhao M T, Singh B P, Prasad P N. J. Chem. Phys., 1988, 89 (9): 5535.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133