Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation

Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Axially chiral 2,2′-methylenedioxy-bridged-1,1′-binaphthyls, quaternaphthalenes, and octinaphthalenes were synthesized and their optical properties researched. 2,2′-Methylenedioxy bridges led to a continuous extremely cisoid conformation and subsequent extensive conjugation in the rod direction. Therefore, the absorption and fluorescence regions were red-shifted as the number of naphthalene rings increased. These oligonaphthalenes fluoresced in both solution and the solid state. Furthermore, DFT calculations showed that the LUMO and HOMO of these bridged oligonaphthalenes were spread over a wide range.

Original languageEnglish
Pages (from-to)1832-1835
Number of pages4
JournalOrganic Letters
Volume12
Issue number8
DOIs
Publication statusPublished - Apr 16 2010
Externally publishedYes

Fingerprint

conjugation
oligomers
Oligomers
naphthalene
Discrete Fourier transforms
Conformations
rods
Optical properties
Fluorescence
solid state
optical properties
fluorescence
rings
Direction compound

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation. / Takaishi, Kazuto; Kawamoto, Masuki; Tsubaki, Kazunori.

In: Organic Letters, Vol. 12, No. 8, 16.04.2010, p. 1832-1835.

Research output: Contribution to journalArticle

Takaishi, Kazuto ; Kawamoto, Masuki ; Tsubaki, Kazunori. / Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation. In: Organic Letters. 2010 ; Vol. 12, No. 8. pp. 1832-1835.
@article{b0ffc796ec394b42b4c2158fda9cbc4b,
title = "Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation",
abstract = "Axially chiral 2,2′-methylenedioxy-bridged-1,1′-binaphthyls, quaternaphthalenes, and octinaphthalenes were synthesized and their optical properties researched. 2,2′-Methylenedioxy bridges led to a continuous extremely cisoid conformation and subsequent extensive conjugation in the rod direction. Therefore, the absorption and fluorescence regions were red-shifted as the number of naphthalene rings increased. These oligonaphthalenes fluoresced in both solution and the solid state. Furthermore, DFT calculations showed that the LUMO and HOMO of these bridged oligonaphthalenes were spread over a wide range.",
author = "Kazuto Takaishi and Masuki Kawamoto and Kazunori Tsubaki",
year = "2010",
month = "4",
day = "16",
doi = "10.1021/ol100582v",
language = "English",
volume = "12",
pages = "1832--1835",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation

AU - Takaishi, Kazuto

AU - Kawamoto, Masuki

AU - Tsubaki, Kazunori

PY - 2010/4/16

Y1 - 2010/4/16

N2 - Axially chiral 2,2′-methylenedioxy-bridged-1,1′-binaphthyls, quaternaphthalenes, and octinaphthalenes were synthesized and their optical properties researched. 2,2′-Methylenedioxy bridges led to a continuous extremely cisoid conformation and subsequent extensive conjugation in the rod direction. Therefore, the absorption and fluorescence regions were red-shifted as the number of naphthalene rings increased. These oligonaphthalenes fluoresced in both solution and the solid state. Furthermore, DFT calculations showed that the LUMO and HOMO of these bridged oligonaphthalenes were spread over a wide range.

AB - Axially chiral 2,2′-methylenedioxy-bridged-1,1′-binaphthyls, quaternaphthalenes, and octinaphthalenes were synthesized and their optical properties researched. 2,2′-Methylenedioxy bridges led to a continuous extremely cisoid conformation and subsequent extensive conjugation in the rod direction. Therefore, the absorption and fluorescence regions were red-shifted as the number of naphthalene rings increased. These oligonaphthalenes fluoresced in both solution and the solid state. Furthermore, DFT calculations showed that the LUMO and HOMO of these bridged oligonaphthalenes were spread over a wide range.

UR - http://www.scopus.com/inward/record.url?scp=77951153225&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951153225&partnerID=8YFLogxK

U2 - 10.1021/ol100582v

DO - 10.1021/ol100582v

M3 - Article

VL - 12

SP - 1832

EP - 1835

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -