Fluorocarbon-modified organic semiconductors: molecular architecture, electronic, and crystal structure tuning of arene- versus fluoroarene-thiophene oligomer thin-film properties

Journal of the American Chemical Society
Myung-Han YoonTobin J Marks

Abstract

We present here the systematic synthesis and comparative physicochemical characterization of a series of regiochemically varied and core size extension-modulated arene(perfluoroarene)-thiophene oligomers. The molecules investigated are: 5,5''-diphenyl-2,2':5',2'':5'',2'''-quaterthiophene (1), 5,5'-bis[1-[4-(thien-2-yl)phenyl]]-2,2'-dithiophene (2), 4,4'-bis[5-(2,2'-dithiophenyl)]-biphenyl (3), 5,5''-diperfluorophenyl-2,2':5',2'':5'',2'''-quaterthiophene (4), 5,5'-bis[1-[4-(thien-2-yl)perfluorophenyl]]-2,2'-dithiophene (5), 4,4'-bis[5-(2,2'-dithiophenyl)]-perfluorobiphenyl (6), 5,5''-diperfluorophenyl-2,2':5',2''-tertthiophene (7), 5,5'-diperfluorophenyl-2,2'-dihiophene (8), and 5,5-diperfluorophenylthiophene (9). Trends in optical absorption and emission parameters, molecular structures as defined by single-crystal X-ray diffraction, as well as electrochemical redox processes are described. The morphologies and microstructures of the vapor-deposited films grown over a range of growth temperatures have also been characterized. Field-effect transistor (FET) measurements demonstrate that all of these materials are FET-active and, depending on the molecular architecture, exhibit comparably good p- or n-type mobility when optimum fi...Continue Reading

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Citations

May 28, 2011·Accounts of Chemical Research·Hakan UstaTobin J Marks
Jun 30, 2010·Chemical Communications : Chem Comm·Huanli DongWenping Hu
Feb 20, 2016·The Journal of Organic Chemistry·Asik HossianRanjan Jana
Dec 14, 2016·The Journal of Physical Chemistry Letters·Begoña Milián-Medina, Johannes Gierschner
Mar 27, 2007·The Journal of Chemical Physics·Begoña Milián MedinaJohannes Gierschner
Dec 1, 2015·Chemistry : a European Journal·Karlee P CastroOlga V Boltalina
May 4, 2010·Advanced Materials·Yugeng Wen, Yunqi Liu
Apr 10, 2009·Journal of the American Chemical Society·Rüdiger SchmidtFrank Würthner
Sep 30, 2017·Advanced Materials·Eun Kwang LeeJoon Hak Oh
Jun 7, 2016·Physical Chemistry Chemical Physics : PCCP·Benedikt DänekampJohannes Gierschner
Mar 19, 2015·Physical Chemistry Chemical Physics : PCCP·L ColellaC Bertarelli
Nov 30, 2018·Chemical Communications : Chem Comm·C A Gunawardana, C B Aakeröy
Oct 13, 2007·Chemistry : a European Journal·Silvia AlesiGiovanna Barbarella
Dec 7, 2007·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Manuela MelucciGiovanna Barbarella
Jul 24, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Take-aki KoizumiTakakazu Yamamoto
Jan 10, 2009·Chemistry : a European Journal·Silvia AlesiGiovanna Barbarella
Apr 30, 2009·Angewandte Chemie·Thomas K WoodMasood Parvez
Apr 17, 2010·Chemical Society Reviews·Hagen Klauk
Jan 3, 2020·Physical Chemistry Chemical Physics : PCCP·Ekaterina A KomissarovaDmitry Yu Paraschuk
Jan 22, 2008·Soft Matter·Manuela SchiekHorst-Günter Rubahn
Jun 28, 2012·Physical Chemistry Chemical Physics : PCCP·Xiaolan QiaoDonghang Yan
Nov 17, 2011·Angewandte Chemie·Peng HuWeiping Su
Mar 8, 2011·Advanced Materials·Lang JiangWenping Hu
Sep 27, 2014·Angewandte Chemie·Yasutomo SegawaKenichiro Itami
Jun 12, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Claas HoffendMatthias Wagner

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