Res. Chem. Intermed.
, Vol. 34, No. 2–3, pp. 257–266 (2008)
Koninklijke Brill NV, Leiden, 2008.
Also available online - www.brill.nl/rci
New ﬂuorescent benzocrown ether derivatives of
tetrathiafulvalene: facile synthesis and
WEI LIU, YUN-JUN GUO, YU-JIA LI, YAN-YAN MAO, JING-LIN ZUO
and XIAO-ZENG YOU
Coordination Chemistry Institute and the State Key Laboratory of Coordination Chemistry,
Nanjing University, Nanjing 210093, P. R. China
Received 20 November 2006; accepted 20 January 2007
Abstract—Two new ﬂuorescent crown ether derivatives of tetrathiafulvalene (TTF) (2a and 2b)were
synthesized and characterized; their electrochemical response to Na
ions and ﬂuorescence properties
were investigated. The mechanism of the strong ﬂuorescence has also been explored.
Keywords: Tetrathiafulvalene; ﬂuorescence; cyclic voltammetry; Na
During the past few years, continued interest has been directed towards chemical
modiﬁcation of different functional groups on the tetrathiafulvalene (TTF) frame-
work, expecting to acquire novel functional materials [1– 14], such as molecular
sensors [15, 16], shuttles [17, 18], switches [19–22] and photovoltaic materials
[23–27]. TTF and its derivatives have unique ability to supply electrons efﬁciently
and can be switched reversibly in three redox states (0/+1/+2) through oxida-
tion/reduction [28, 29]. Crown annelated TTFs were designed originally for ion
sensing [30–34], and in these systems the uptake and release of guest metal cations
could be monitored electrochemically. Generally, when guest cations combine with
the crown site, the electron density of the TTF will be perturbed, which will cause
a variation of the redox potential.
Very recently, we have described a 15-membered O,S-hybrid crown ether ﬂuo-
roionophore in which the crown ether recognition site and an anthracene moiety as
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