TY - JOUR
T1 - Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers
AU - Sajoto, Tissa
AU - Tiwari, Shree Prakash
AU - Li, Huifang
AU - Risko, Chad
AU - Barlow, Stephen
AU - Zhang, Qing
AU - Cho, Jian Yang
AU - Brédas, Jean Luc
AU - Kippelen, Bernard
AU - Marder, Seth R.
N1 - Funding Information:
We would like to acknowledge Benjamin Wunsch, Chun Huang, and Sergio Paniagua for acquiring TGA and DSC data. This work was funded by Solvay S.A., the Office of Naval Research , and the STC Program of the National Science Foundation ( DMR-0120967 ).
PY - 2012/2/28
Y1 - 2012/2/28
N2 - A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.
AB - A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.
KW - Conjugated polymers
KW - Electron transport
KW - Naphthalene diimide polymers
UR - http://www.scopus.com/inward/record.url?scp=84862777751&partnerID=8YFLogxK
U2 - 10.1016/j.polymer.2012.01.016
DO - 10.1016/j.polymer.2012.01.016
M3 - Article
AN - SCOPUS:84862777751
SN - 0032-3861
VL - 53
SP - 1072
EP - 1078
JO - Polymer
JF - Polymer
IS - 5
ER -