A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene

Dmitrii F. Perepichka, Michael Bendikov, Hong Meng, Fred Wudl

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.

Original languageEnglish
Pages (from-to)10190-10191
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number34
DOIs
Publication statusPublished - Aug 27 2003

Fingerprint

Dechlorination
Cyclization
Ladders
Polymers
Carbon
Molecules
Temperature
pentacene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene. / Perepichka, Dmitrii F.; Bendikov, Michael; Meng, Hong; Wudl, Fred.

In: Journal of the American Chemical Society, Vol. 125, No. 34, 27.08.2003, p. 10190-10191.

Research output: Contribution to journalArticle

@article{aa0402ceb28b49179f96caeac65ada5d,
title = "A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene",
abstract = "We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.",
author = "Perepichka, {Dmitrii F.} and Michael Bendikov and Hong Meng and Fred Wudl",
year = "2003",
month = "8",
day = "27",
doi = "10.1021/ja036193i",
language = "English",
volume = "125",
pages = "10190--10191",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "34",

}

TY - JOUR

T1 - A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene

AU - Perepichka, Dmitrii F.

AU - Bendikov, Michael

AU - Meng, Hong

AU - Wudl, Fred

PY - 2003/8/27

Y1 - 2003/8/27

N2 - We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.

AB - We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.

UR - http://www.scopus.com/inward/record.url?scp=0041429625&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0041429625&partnerID=8YFLogxK

U2 - 10.1021/ja036193i

DO - 10.1021/ja036193i

M3 - Article

VL - 125

SP - 10190

EP - 10191

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 34

ER -