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O
H
N
N
H
O
hv
solid
O
H
N
O H
N
H
O
N
H
O
N
O H
N
N
H
O
Scheme 7.7
From our studies, co-crystallization of 1,4-bpeb with
4-benzylresorcinol (4-bn-res) was determined to generate a
discrete four-component assembly with 1,4-bpeb positioned for
a double [2 + 2] photodimerization, with the closest separation
betweenC=Cbondsofadjacentassembliesbeing5.4Å(Fig.7.3a)
[24]. UV irradiation of 2(4-bn-res)·2(1,4-bpeb) produced 4,4
-tppcp
inquantitativeyield.Thestructureofthecyclophanewasconfirmed
viasingle-crystalX-raydifraction.
24
(a)
5.4 Å
(b)
Figure 7.3
X-ray structures of (a) (4-bn-res)(1,4-bpeb) and (b) 4,4
-
tppcp.
In addition to a paracyclophane, we anticipated that a res could
be used to construct [
= 3 or 5). Ladderanes had
previously been discovered in intracellular membrane lipids of
anammox
n
]-ladderanes (
n
bacteria, which are known to participate in the oceanic
N
suggested
that a template-controlled [2 + 2] photodimerization involving
the conjugated diene
cycle [25]. A retrosynthetic analysis of a ladderane
2
trans,trans
-1,4-bis(4-pyridyl)-1,3-butadiene
 
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