Synthesis and Characterization of Polysubstituted Dibenzopyrenes as Charge-Transporting Materials

被引:10
作者
Kumar, Sushil [1 ]
Ho, Man-Tzu [1 ]
Tao, Yu-Tai [1 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
关键词
FIELD-EFFECT TRANSISTORS; HIGH-PERFORMANCE; SCHOLL REACTION; ORGANIC SEMICONDUCTOR; HIGH-MOBILITY; N-CHANNEL; DERIVATIVES; DEPENDENCE; POLYMERS; ACCEPTOR;
D O I
10.1021/acs.orglett.6b02354
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of benzopyrene-based semiconducting molecules is prepared and characterized. A four-step protocol involving Suzuki coupling and aromatic dehydrogenation reactions renders the new unsymmetrical framework. Introduction of various substituents at the dibenzopyrene framework modulates mainly the optoelectronic properties rather than the packing motif. Single-crystal field-effect transistors fabricated from these materials show a mobility ranging from 0.7 to 3.2 cm(2)/(V s). The highest mobility, 3.2 cm(2)/(V s), with an on/off ratio of 10(4)-10(5) was achieved for 11-methoxy-8-(4-methoxyphenyl)dibenzo-[a,e]pyrene.
引用
收藏
页码:4876 / 4879
页数:4
相关论文
共 42 条
[1]   High mobility single-crystal field-effect transistors from bisindoloquinoline semiconductors [J].
Ahmed, Eilaf ;
Briseno, Alejandro L. ;
Xia, Younan ;
Jenekhe, Samson A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1118-+
[2]   Benzobisthiazole-Thiophene Copolymer Semiconductors: Synthesis, Enhanced Stability, Field-Effect Transistors, and Efficient Solar Cells [J].
Ahmed, Eilaf ;
Kim, Felix S. ;
Xin, Hao ;
Jenekhe, Samson A. .
MACROMOLECULES, 2009, 42 (22) :8615-8618
[3]   Tailoring Structure-Property Relationships in Dithienosilole-Benzothiadiazole Donor-Acceptor Copolymers [J].
Beaujuge, Pierre M. ;
Pisula, Wojciech ;
Tsao, Hoi Nok ;
Ellinger, Stefan ;
Muellen, Klaus ;
Reynolds, John R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7514-+
[4]   Importance of intermolecular interactions in assessing hopping mobilities in organic field effect transistors: Pentacene versus dithiophene-tetrathiafulvalene [J].
Bromley, ST ;
Mas-Torrent, M ;
Hadley, P ;
Rovira, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6544-6545
[5]   Very Low Degree of Energetic Disorder as the Origin of High Mobility in an n-channel Polymer Semiconductor [J].
Caironi, Mario ;
Bird, Matt ;
Fazzi, Daniele ;
Chen, Zhihua ;
Di Pietro, Riccardo ;
Newman, Christopher ;
Facchetti, Antonio ;
Sirringhaus, Henning .
ADVANCED FUNCTIONAL MATERIALS, 2011, 21 (17) :3371-3381
[6]   Nonvolatile transistor memory devices using high dielectric constant polyimide electrets [J].
Chou, Ying-Hsuan ;
Yen, Hung-Ju ;
Tsai, Chia-Liang ;
Lee, Wen-Ya ;
Liou, Guey-Sheng ;
Chen, Wen-Chang .
JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (19) :3235-3243
[7]  
Clar E, 1943, BER DTSCH CHEM GES, V76, P611
[8]   Charge transport in organic semiconductors [J].
Coropceanu, Veaceslav ;
Cornil, Jerome ;
da Silva Filho, Demetrio A. ;
Olivier, Yoann ;
Silbey, Robert ;
Bredas, Jean-Luc .
CHEMICAL REVIEWS, 2007, 107 (04) :926-952
[9]   ExCage [J].
Dale, Edward J. ;
Vermeulen, Nicolaas A. ;
Thomas, Andy A. ;
Barnes, Jonathan C. ;
Juricek, Michal ;
Blackburn, Anthea K. ;
Strutt, Nathan L. ;
Sarjeant, Amy A. ;
Stern, Charlotte L. ;
Denmark, Scott E. ;
Stoddart, J. Fraser .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (30) :10669-10682
[10]   Morphology directing synthesis of benzo[a]pyrene microstructures and their photo physical properties [J].
Das, Debasish ;
Sahoo, Gobinda P. ;
Mazumdar, Prativa ;
Maity, Asim ;
Chattopadhyay, Dipankar ;
Salgado-Moran, Guillermo ;
Misra, Ajay .
JOURNAL OF MOLECULAR LIQUIDS, 2015, 206 :47-55