Transcript Synthesis and photophysical properties of pyrene-based light

Department of Chemistry
Seminar Announcement
Date/Time/Venue
Title/Speaker
11 Mar (Fri)
3pm – 4pm
Synthesis and photophysical properties of pyrenebased light-emitting monomers: highly blue
fluorescent multiply-conjugated-shaped
architectures
@ S8 Level 3
Executive
Classroom
Professor Takehiko Yamato
Saga University, Japan
Host : Asst Prof Wu Jishan
About the Speaker
Professor Takehito Yamato (大和武彦) was born in Fukuoka, Japan in 1953.
He graduated in 1975 with a BS from Kyushu Institute of Technology and
thereafter in 1983 with a PhD from Kyushu University. He carried out his
postdoctoral research at State University of New York at Stony Brook with
Prof Iwao Ojima and University of Southern California with Prof G A Olah,
Novel prize 1995 (1983-1985).
He joined the faculty in the Department of Applied Chemistry at Saga
University in 1986 and is currently a Professor of Chemistry. His research
field focuses on synthetic organic chemistry, supramolecular chemistry and
development of OLED materials.
Abstract
Recently, pyrene derivatives have been turned out to be promising candidates for several
applications like organic light-emitting diodes (OLEDs) due to its desirable photophysical properties.
Previously we have reported the syntheses of series of pyrene-based blue light-emitting monomers
using the tert-butyl group as a positional protective function.1,2 In this talk we will discuss the synthesis
and photophysical properties of new series of pyrene-based cruciform-shaped -conjugated
monomers as well as the relationship between the substituents and positions.3,4
A new series of pyrene-based, highly pure blue
fluorescent and stable monomers, namely 2,7-di-tert- butyl4,5,9,10-tetrakis(p-substituted phenylethynyl)pyrenes, have
been successfully synthesized via a Pd/Cu-catalysed
Sonogashira coupling reaction in excellent yield. As
revealed from single-crystal X-ray analysis, there is a
herring-bone pattern between stacked columns but the -
stacking distance (ca. 5.82 Å) of adjacent two pyrene units
are not especially short at ca. 3.50–3.70 Å due to the
introduction of the two bulky tert-butyl groups in pyrene
rings at 2 and 7 positions. Their photophysical properties
were carefully examined in different organic solvents and
these data strongly indicate their promising application as
blue-emitting materials in organic light-emitting diodes
(OLEDs).
[1] T. Yamato, M. Fujimoto, A. Miyazawa and K. Matsuo, J. Chem. Soc.
Perkin Trans. 1, 1201 (1997).
[2] T. Yamato, S. Miyamoto, T. Hironaka and Y. Miura, Org. Lett., 7, 3
(2005).
[3] J. Hu, M. Era, M.R.J. Elsegood and T. Yamato, Eur. J. Org. Chem.,
2010, 72–79.
[4] X. Ni, S. Wang, X. Zeng, Z. Tao and T. Yamato, Org. Lett. in press.
All are Welcome
R
R
10
4
9
5
R
R
1 a: R = H (65%)
b: R = t-Bu (68%)
c: R = OMe (75%)
X-ray structure of 1c