Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds

Hitoshi Muguruma, Takashi Saito, Satoshi Sasaki, Shu Hotta, Isao Karube

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.

Original languageEnglish
Pages (from-to)173-178
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume33
Issue number1
Publication statusPublished - 1996
Externally publishedYes

Fingerprint

Thiophenes
Electronic properties
Dimers
Polymerization
Water

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds. / Muguruma, Hitoshi; Saito, Takashi; Sasaki, Satoshi; Hotta, Shu; Karube, Isao.

In: Journal of Heterocyclic Chemistry, Vol. 33, No. 1, 1996, p. 173-178.

Research output: Contribution to journalArticle

Muguruma, Hitoshi ; Saito, Takashi ; Sasaki, Satoshi ; Hotta, Shu ; Karube, Isao. / Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds. In: Journal of Heterocyclic Chemistry. 1996 ; Vol. 33, No. 1. pp. 173-178.
@article{d7447540bcc5495581a4b8a477dc4c83,
title = "Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds",
abstract = "We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.",
author = "Hitoshi Muguruma and Takashi Saito and Satoshi Sasaki and Shu Hotta and Isao Karube",
year = "1996",
language = "English",
volume = "33",
pages = "173--178",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "1",

}

TY - JOUR

T1 - Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds

AU - Muguruma, Hitoshi

AU - Saito, Takashi

AU - Sasaki, Satoshi

AU - Hotta, Shu

AU - Karube, Isao

PY - 1996

Y1 - 1996

N2 - We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.

AB - We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.

UR - http://www.scopus.com/inward/record.url?scp=0000244229&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000244229&partnerID=8YFLogxK

M3 - Article

VL - 33

SP - 173

EP - 178

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 1

ER -