Annelated, chiral π-conjugated systems: Tetraphenylenes and helical β-oligothiophenes

Andrzej Rajca, Suchada Rajca, Maren Pink, Makoto Miyasaka

Research output: Contribution to journalArticle

75 Citations (Scopus)

Abstract

Compounds with highly annelated, chiral π-systems, such as tetraphenylenes and [n]helicenes, are known to possess strong chiral properties and high configurational stability, which are prerequisites for many chiral materials. This account describes the unfolding story about our research on the synthesis and X-ray crystallographic characterization of functionalized nonracemic tetraphenylenes and helical β-oligothiophenes, as well as related [n]helicene derivatives. 1 Introduction 1.1 Riley' s Three-Dimensional Graphite 1.2 Annelated Helical β-Oligothiophenes: Carbon-Sulfur [n]Helicenes 2 Tetraarylenes 2.1 Double Helical Octaphenylene 2.2 Biphenylene Dimer 2.3 Enantiopure Tetranaphthylene: Binaphthyl Dimer 2.4 Asymmetric Synthesis of Tetraphenylenes: Greek Cross Dodecaphenylene 3 Synthesis of Annelated Helical β-Oligothiophenes 3.1 [7]Helicene 3.2 [7]Helicene: McMurry Reaction 3.3 [11]Helicene 3.4 Toward [n]Helicenes with n >11: Progress Report 4 Discovery of Conjoined Double Helicenes 5 Future Directions.

Original languageEnglish (US)
Pages (from-to)1799-1822
Number of pages24
JournalSynlett
Issue number12
DOIs
StatePublished - Jul 24 2007

Fingerprint

Dimers
Graphite
Sulfur
Carbon
Derivatives
X rays
helicenes
Direction compound

Keywords

  • Asymmetric synthesis
  • Chirality
  • Coupling
  • Enantiomeric resolution
  • Kinetic resolution

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Annelated, chiral π-conjugated systems : Tetraphenylenes and helical β-oligothiophenes. / Rajca, Andrzej; Rajca, Suchada; Pink, Maren; Miyasaka, Makoto.

In: Synlett, No. 12, 24.07.2007, p. 1799-1822.

Research output: Contribution to journalArticle

@article{a4d65dbb8bac45acae1cf3efe4a3bdb4,
title = "Annelated, chiral π-conjugated systems: Tetraphenylenes and helical β-oligothiophenes",
abstract = "Compounds with highly annelated, chiral π-systems, such as tetraphenylenes and [n]helicenes, are known to possess strong chiral properties and high configurational stability, which are prerequisites for many chiral materials. This account describes the unfolding story about our research on the synthesis and X-ray crystallographic characterization of functionalized nonracemic tetraphenylenes and helical β-oligothiophenes, as well as related [n]helicene derivatives. 1 Introduction 1.1 Riley' s Three-Dimensional Graphite 1.2 Annelated Helical β-Oligothiophenes: Carbon-Sulfur [n]Helicenes 2 Tetraarylenes 2.1 Double Helical Octaphenylene 2.2 Biphenylene Dimer 2.3 Enantiopure Tetranaphthylene: Binaphthyl Dimer 2.4 Asymmetric Synthesis of Tetraphenylenes: Greek Cross Dodecaphenylene 3 Synthesis of Annelated Helical β-Oligothiophenes 3.1 [7]Helicene 3.2 [7]Helicene: McMurry Reaction 3.3 [11]Helicene 3.4 Toward [n]Helicenes with n >11: Progress Report 4 Discovery of Conjoined Double Helicenes 5 Future Directions.",
keywords = "Asymmetric synthesis, Chirality, Coupling, Enantiomeric resolution, Kinetic resolution",
author = "Andrzej Rajca and Suchada Rajca and Maren Pink and Makoto Miyasaka",
year = "2007",
month = "7",
day = "24",
doi = "10.1055/s-2007-984538",
language = "English (US)",
pages = "1799--1822",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "12",

}

TY - JOUR

T1 - Annelated, chiral π-conjugated systems

T2 - Tetraphenylenes and helical β-oligothiophenes

AU - Rajca, Andrzej

AU - Rajca, Suchada

AU - Pink, Maren

AU - Miyasaka, Makoto

PY - 2007/7/24

Y1 - 2007/7/24

N2 - Compounds with highly annelated, chiral π-systems, such as tetraphenylenes and [n]helicenes, are known to possess strong chiral properties and high configurational stability, which are prerequisites for many chiral materials. This account describes the unfolding story about our research on the synthesis and X-ray crystallographic characterization of functionalized nonracemic tetraphenylenes and helical β-oligothiophenes, as well as related [n]helicene derivatives. 1 Introduction 1.1 Riley' s Three-Dimensional Graphite 1.2 Annelated Helical β-Oligothiophenes: Carbon-Sulfur [n]Helicenes 2 Tetraarylenes 2.1 Double Helical Octaphenylene 2.2 Biphenylene Dimer 2.3 Enantiopure Tetranaphthylene: Binaphthyl Dimer 2.4 Asymmetric Synthesis of Tetraphenylenes: Greek Cross Dodecaphenylene 3 Synthesis of Annelated Helical β-Oligothiophenes 3.1 [7]Helicene 3.2 [7]Helicene: McMurry Reaction 3.3 [11]Helicene 3.4 Toward [n]Helicenes with n >11: Progress Report 4 Discovery of Conjoined Double Helicenes 5 Future Directions.

AB - Compounds with highly annelated, chiral π-systems, such as tetraphenylenes and [n]helicenes, are known to possess strong chiral properties and high configurational stability, which are prerequisites for many chiral materials. This account describes the unfolding story about our research on the synthesis and X-ray crystallographic characterization of functionalized nonracemic tetraphenylenes and helical β-oligothiophenes, as well as related [n]helicene derivatives. 1 Introduction 1.1 Riley' s Three-Dimensional Graphite 1.2 Annelated Helical β-Oligothiophenes: Carbon-Sulfur [n]Helicenes 2 Tetraarylenes 2.1 Double Helical Octaphenylene 2.2 Biphenylene Dimer 2.3 Enantiopure Tetranaphthylene: Binaphthyl Dimer 2.4 Asymmetric Synthesis of Tetraphenylenes: Greek Cross Dodecaphenylene 3 Synthesis of Annelated Helical β-Oligothiophenes 3.1 [7]Helicene 3.2 [7]Helicene: McMurry Reaction 3.3 [11]Helicene 3.4 Toward [n]Helicenes with n >11: Progress Report 4 Discovery of Conjoined Double Helicenes 5 Future Directions.

KW - Asymmetric synthesis

KW - Chirality

KW - Coupling

KW - Enantiomeric resolution

KW - Kinetic resolution

UR - http://www.scopus.com/inward/record.url?scp=34547624725&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547624725&partnerID=8YFLogxK

U2 - 10.1055/s-2007-984538

DO - 10.1055/s-2007-984538

M3 - Article

AN - SCOPUS:34547624725

SP - 1799

EP - 1822

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 12

ER -