TY - JOUR
T1 - Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes
AU - Chang, Shao Ling
AU - Lu, Chih Wen
AU - Lai, Yu Ying
AU - Hsu, Jhih Yang
AU - Cheng, Yen-Ju
PY - 2016/2/5
Y1 - 2016/2/5
N2 -
Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl
2
-catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10
-2
cm
2
V
-1
s
-1
.
AB -
Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl
2
-catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10
-2
cm
2
V
-1
s
-1
.
UR - http://www.scopus.com/inward/record.url?scp=84957881304&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5b03294
DO - 10.1021/acs.orglett.5b03294
M3 - Article
AN - SCOPUS:84957881304
VL - 18
SP - 368
EP - 371
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 3
ER -