TY - JOUR
T1 - The first solution-processable n-type phthalocyaninato copper semiconductor
T2 - Tuning the semiconducting nature via peripheral electron-withdrawing octyloxycarbonyl substituents
AU - Ma, Pan
AU - Kan, Jinglan
AU - Zhang, Yuexing
AU - Hang, Chunhua
AU - Bian, Yongzhong
AU - Chen, Yanli
AU - Kobayshi, Nagao
AU - Jiang, Jianzhuang
PY - 2011/12/14
Y1 - 2011/12/14
N2 - A series of unsymmetrical phthalocyaninato copper complexes simultaneously incorporating electron-withdrawing and electron-donating substituents at the phthalocyanine periphery Cu{Pc(15C5)[(COOC8H17) 6]} (2), Cu{Pc[(adj-15C5)2][(COOC8H 17)4]} (3), Cu{Pc[(opp-15C5)2][(COOC 8H17)4]} (4), Cu{Pc(15C5) 3[(COOC8H17)2]} (5) were prepared and isolated. For comparative studies, symmetrical analogues including 2,3,9,10,16,17,24,25-octakis(octyloxycarbonyl)phthalocyaninato copper complex Cu[Pc(COOC8H17)8] (1) and 2,3,9,10,16,17,24,25- tetrakis(15-crown-5)phthalocyaninato copper complex Cu[Pc(15C5)4] (6) were also prepared. Their electrochemistry was studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). With the help of a solution-based self-assembly process, these compounds were fabricated into organic field effect transistors (OFETs) with top contact configuration on hexamethyldisilazane (HMDS)-treated SiO2/Si substrate. In line with the electrochemical investigation results, a p-type OFET with a carrier mobility (for holes) of 0.06 cm2 V-1 s-1 was shown for Cu[Pc(15C5)4] (6) with electron-donating 15-crown-5 as the sole type of peripheral substituent. In contrast, n-type devices with a carrier mobility (for electrons) of 6.7 × 10-6-1.6 × 10-4 cm2 V-1 s-1 were achieved for 1-5 with electron-withdrawing octyloxycarbonyl substituents at the peripheral positions of phthalocyanine ring, indicating the significant effect of electron-withdrawing octyloxycarbonyl substituents on tuning the nature of phthalocyanine organic semiconductors. The present results represent the first example of solution-processed n-type phthalocyanine-based OFET devices.
AB - A series of unsymmetrical phthalocyaninato copper complexes simultaneously incorporating electron-withdrawing and electron-donating substituents at the phthalocyanine periphery Cu{Pc(15C5)[(COOC8H17) 6]} (2), Cu{Pc[(adj-15C5)2][(COOC8H 17)4]} (3), Cu{Pc[(opp-15C5)2][(COOC 8H17)4]} (4), Cu{Pc(15C5) 3[(COOC8H17)2]} (5) were prepared and isolated. For comparative studies, symmetrical analogues including 2,3,9,10,16,17,24,25-octakis(octyloxycarbonyl)phthalocyaninato copper complex Cu[Pc(COOC8H17)8] (1) and 2,3,9,10,16,17,24,25- tetrakis(15-crown-5)phthalocyaninato copper complex Cu[Pc(15C5)4] (6) were also prepared. Their electrochemistry was studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). With the help of a solution-based self-assembly process, these compounds were fabricated into organic field effect transistors (OFETs) with top contact configuration on hexamethyldisilazane (HMDS)-treated SiO2/Si substrate. In line with the electrochemical investigation results, a p-type OFET with a carrier mobility (for holes) of 0.06 cm2 V-1 s-1 was shown for Cu[Pc(15C5)4] (6) with electron-donating 15-crown-5 as the sole type of peripheral substituent. In contrast, n-type devices with a carrier mobility (for electrons) of 6.7 × 10-6-1.6 × 10-4 cm2 V-1 s-1 were achieved for 1-5 with electron-withdrawing octyloxycarbonyl substituents at the peripheral positions of phthalocyanine ring, indicating the significant effect of electron-withdrawing octyloxycarbonyl substituents on tuning the nature of phthalocyanine organic semiconductors. The present results represent the first example of solution-processed n-type phthalocyanine-based OFET devices.
UR - http://www.scopus.com/inward/record.url?scp=81255150700&partnerID=8YFLogxK
U2 - 10.1039/c1jm13082j
DO - 10.1039/c1jm13082j
M3 - Article
AN - SCOPUS:81255150700
SN - 0959-9428
VL - 21
SP - 18552
EP - 18559
JO - Journal of Materials Chemistry
JF - Journal of Materials Chemistry
IS - 46
ER -