TY - JOUR
T1 - Thieno[3,4-c]pyrrole-incorporated quinoidal terthiophene with dicyanomethylene termini
T2 - Synthesis, characterization, and redox properties
AU - Takeda, Kyoko
AU - Shimawaki, Masafumi
AU - Nakao, Akiko
AU - Osaka, Itaru
AU - Miyazaki, Eigo
AU - Takimiya, Kazuo
PY - 2010/8/18
Y1 - 2010/8/18
N2 - Synthesis, characterization, molecular structure, and redox properties of a new quinoidal terthiophene incorporated with a thieno[3,4-c]pyrrole moiety (5) are described. Although an electrochemical reduction of 5 formally produces the non-classical thieno[3,4-c]pyrrole moiety, 5 showed a reversible reduction wave on cyclic voltammogram, indicating that the thieno[3,4-c]pyrrole moiety can be stabilized by delocalized 10π-conjugated system in the dianion state of 5. However, the reduction potential was largely affected by incorporation of the thieno[3,4-c]pyrrole and shifted cathodically by 0.4 V compared to that of the parent quinodial terthiophene (1).
AB - Synthesis, characterization, molecular structure, and redox properties of a new quinoidal terthiophene incorporated with a thieno[3,4-c]pyrrole moiety (5) are described. Although an electrochemical reduction of 5 formally produces the non-classical thieno[3,4-c]pyrrole moiety, 5 showed a reversible reduction wave on cyclic voltammogram, indicating that the thieno[3,4-c]pyrrole moiety can be stabilized by delocalized 10π-conjugated system in the dianion state of 5. However, the reduction potential was largely affected by incorporation of the thieno[3,4-c]pyrrole and shifted cathodically by 0.4 V compared to that of the parent quinodial terthiophene (1).
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U2 - 10.1016/j.tetlet.2010.06.052
DO - 10.1016/j.tetlet.2010.06.052
M3 - Article
AN - SCOPUS:77955425116
VL - 51
SP - 4375
EP - 4377
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 33
ER -