J . L I E , Y . X I O N G , Q . WU , S . WA N G , X . G A O , H . L I * ( S H A N G H A I I N S T I T U T E O F O R G A N I C
Ca t e g o r y
C H E M I S T R Y, P. R . O F C H I N A )
Synthesis of
Materials and
Unnatural Products
Synthesis and Physicochemical Properties of Strong Electron Acceptor 14,14,15,15-Tetracyano-6,13pentacenequinodimethane (TCPQ) Diimide
Eur. J. Org. Chem. 2012, 6136–6139.
Ke y w o rd s
Electron-Acceptor Pentacene Derivative
pentacenes
cycloaddition
tetracyanoquinodimethanes
O
Et
O
1. H2N
O
n-Bu
N
O
Et2O, reflux, 6h
2. Ac2O, Et3N, Ni(OAc)2
O
O
O
88% yield
92% yield
O Et
O Et
n-Bu
S8
NBS, BPO
N
Br
Cl4C, reflux, 4 h
210 °C, 6 h
n-Bu
Br
N
O
O
87% yield
78% yield
O
n-Bu O
NaI,
O
O
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+
O Et
n-Bu, DMF
O Et
n-Bu
Et
N
N
DMF, 110 °C, 3 d
O
O
O
20% yield
NC
CN
n-Bu O
NC
CN
O Et
n-Bu
Et
N
TiCl4, py, CHCl3, reflux, 2 d
N
O
O
NC
CN
1 36% yield
Significance: This paper reports the synthesis of
an extended tetracyanoquinodimethane (TCNQ)
analogue, 1. Although this is not the first report of
a TCNQ-like acene, the method reported by the
authors consists of only six steps, including a
double Diels–Alder reaction and a Knoevenagel
condensation as key steps. The presence of the
diimide substituents not only increases the solubility of the final molecule, but also has implications on its electronic properties.
Comment: Electron-acceptor molecules are essential in organic electronic materials, and an important property of such molecules is the LUMO
energy level. The authors report a LUMO level of
–4.03 eV for 1, which makes this molecule and
derivatives of it, good candidates for a variety of
applications.
SYNFACTS Contributors: Timothy M. Swager, Silvia V. Rocha
Synfacts 0312013, 9(1), 0045 Published online: 17.12.20121861-19581861-194X
DOI: 10.1055/s-0032-1317885; Reg-No.: S13312SF
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