Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness

Masahito Murai; Shinji Iba; Hiromi Ota; Kazuhiko Takai

doi:10.1021/acs.orglett.7b02729

Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness

Masahito Murai, Shinji Iba, Hiromi Ota, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Azulene-fused polycyclic aromatic hydrocarbons (PAHs) were synthesized from commercially available azulene in four steps. The resulting azulene conjugates exhibited significantly narrow HOMO-LUMO bandgaps with high air stability, confirmed by photophysical study. Introduction of azulene also enabled the unique reversible stimuli-responsiveness even with the weak acid and base, which can potentially control the degree of conjugation and optoelectronic properties by simple acid-base and redox processes.

Original language	English
Pages (from-to)	5585-5588
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.7b02729
Publication status	Published - Oct 20 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b02729

Fingerprint Dive into the research topics of 'Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness'. Together they form a unique fingerprint.

Cite this

@article{3bc914064f5c4ae1ba0897d2056b1e17,

title = "Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness",

abstract = "Azulene-fused polycyclic aromatic hydrocarbons (PAHs) were synthesized from commercially available azulene in four steps. The resulting azulene conjugates exhibited significantly narrow HOMO-LUMO bandgaps with high air stability, confirmed by photophysical study. Introduction of azulene also enabled the unique reversible stimuli-responsiveness even with the weak acid and base, which can potentially control the degree of conjugation and optoelectronic properties by simple acid-base and redox processes.",

author = "Masahito Murai and Shinji Iba and Hiromi Ota and Kazuhiko Takai",

year = "2017",

month = oct,

day = "20",

doi = "10.1021/acs.orglett.7b02729",

language = "English",

volume = "19",

pages = "5585--5588",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness

AU - Murai, Masahito

AU - Iba, Shinji

AU - Ota, Hiromi

AU - Takai, Kazuhiko

PY - 2017/10/20

Y1 - 2017/10/20

N2 - Azulene-fused polycyclic aromatic hydrocarbons (PAHs) were synthesized from commercially available azulene in four steps. The resulting azulene conjugates exhibited significantly narrow HOMO-LUMO bandgaps with high air stability, confirmed by photophysical study. Introduction of azulene also enabled the unique reversible stimuli-responsiveness even with the weak acid and base, which can potentially control the degree of conjugation and optoelectronic properties by simple acid-base and redox processes.

AB - Azulene-fused polycyclic aromatic hydrocarbons (PAHs) were synthesized from commercially available azulene in four steps. The resulting azulene conjugates exhibited significantly narrow HOMO-LUMO bandgaps with high air stability, confirmed by photophysical study. Introduction of azulene also enabled the unique reversible stimuli-responsiveness even with the weak acid and base, which can potentially control the degree of conjugation and optoelectronic properties by simple acid-base and redox processes.

UR - http://www.scopus.com/inward/record.url?scp=85031825624&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85031825624&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b02729

DO - 10.1021/acs.orglett.7b02729

M3 - Article

C2 - 28980817

AN - SCOPUS:85031825624

VL - 19

SP - 5585

EP - 5588

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -