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
N1 - Funding Information:
This work was partially supported by Grants-in-Aid for Scientific Research (No. 20350088) from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and Seeds Excavation Program from Japan Science and Technology Agency (JST) of Japan.
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 -