Synthesis of nano-scale shape-persistent macrocycles via hydrogen bonding-promoted formation of amide and hydrazone bonds

Article abstract of DOI:10.1016/j.tet.2014.06.113

This paper describes the synthesis of two series of rigid macrocycles from hydrogen bonding-induced folded aryl amide and hydrazone oligomers that bear two amines or one amine and one aldehyde. The diamines reacted with diacyl chloride to produce amide macrocycles, whereas the latter underwent self-coupling reactions to afford imine macrocycles. DFT calculations revealed that the new macrocycles possess rigid planar conformations and their cavity diameters were estimated to be 1.86 nm-2.75 nm.

Full text of DOI:10.1016/j.tet.2014.06.113

Tetrahedron 70 (2014) 5483e5487
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Tetrahedron
journal homepage: www.elsevier.com/locate/tet
Synthesis of nano-scale shape-persistent macrocycles via hydrogen
bonding-promoted formation of amide and hydrazone bonds
,
a
Yuan-Yuan Chen a, Lu Wang b, Liang Zhang a, Jiang Zhu c , Hui Wang ,
*
,
a,
*
Dan-Wei Zhang a , Zhan-Ting Li
*
a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
c School of Basic Medical Science, North Sichuan Medical College, Nanchong 637007, China
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 30 April 2014
Received in revised form 20 June 2014
Accepted 26 June 2014
Available online 30 June 2014
This paper describes the synthesis of two series of rigid macrocycles from hydrogen bonding-induced
folded aryl amide and hydrazone oligomers that bear two amines or one amine and one aldehyde.
The diamines reacted with diacyl chloride to produce amide macrocycles, whereas the latter underwent
self-coupling reactions to afford imine macrocycles. DFT calculations revealed that the new macrocycles
possess rigid planar conformations and their cavity diameters were estimated to be 1.86 nme2.75 nm.
Ó 2014 Elsevier Ltd. All rights reserved.
Keywords:
Macrocycles
Aromatic amide
Aromatic hydrazone
Hydrogen bonding
Preorganization
1. Introduction
desirable for the development of new efficient approaches for
obtaining giant aromatic macrocycles.
Pioneering works by Pedersen, Cram, and Lehn had triggered
continued research on the synthesis of macrocyclic compounds and
their discrete properties.1,2 In particular rigid macrocycles have
received considerable interest due to their predictable cavity and
high co-planarity, which facilitate applications in molecular rec-
ognition and self-assembly.3e16 In the past decade, the pre-
organization of precursors driven by continual intramolecular
hydrogen bonds has been established as a useful strategy for the
construction of aromatic amide, hydrazine, and urea macro-
cycles.13e21 Many of the macrocycles have been revealed to com-
plex molecular or ionic guests of matching size and binding sites or
stack into well-defined supramolecular aggregates.20,21 However,
most of the reported macrocycles of this family have a small cavity.
Examples of giant shape-persistent aromatic amide macrocycles
with nano-scale cavity are relatively limited.17d Given the fact that
shape-persistent giant aromatic macrocycles exhibit unique rec-
ognition, stacking, and photophysical properties,22 it is still
We previously reported the one-pot synthesis of 4-mer and 6-
mer macrocycles from monomeric diamine and diacyl chloride
precursors.20c The yields were generally good to high due to the
existence of continuous intramolecular hydrogen bonds, which
induced the last intermediate to fold for macrocyclization, as ob-
served for other related amide macrocycles.20 We also demon-
strated that, via the formation of imine or hydrazone bonds under
thermodynamic control,23 many 6-mer macrocyclic and capsular
architectures could be prepared in high to quantitative yields.16,21
We herein describe that, by rational design of precursors, two
new series of shape-persistent giant macrocycles, that is,12-mer 1a,
16-mer 1b, 9-mer 2a, and 12-mer 2b (Fig. 1), can be prepared
through the formation of amide or imine bonds from hydrogen
bonded preorganized aromatic or hydrazide segments.
2. Results and discussion
2.1. Synthesis of macrocyles 1a and 1b
Diamines 3 and 4 (Fig. 2) were first prepared for the con-
struction of new macrocycles by coupling with diacids. The two
compounds were introduced with four and two sets of three-
* Corresponding authors. Tel.: þ86 21 65643576; fax: þ86 21 65641740; e-mail
addresses: zhujiang312@hotmail.com (J. Zhu), zhangdw@fudan.edu.cn (D.-W.
Zhang), ztli@fudan.edu.cn (Z.-T. Li).
http://dx.doi.org/10.1016/j.tet.2014.06.113
0040-4020/Ó 2014 Elsevier Ltd. All rights reserved.

5484
Y.-Y. Chen et al. / Tetrahedron 70 (2014) 5483e5487
R2N
NR2
R2N
NR2
O
H
O
H
O
H
O
H
O
O
O
O
R2N
O
O
O
NR2
O
R2N
O
O
O
NR2
O
N
N
N
N
O
H
N
O
H
N
O
H
N
O
N
O
O
O
O
H
3
O
O
O
O
O
O
n
O
O
O
O
O
O
H
O
O
O
O
H2N
NR2
NR2
NH2
R2N
H
N
N
N
NR2
NR2
O
O
O
O
O
O
O
1a: n = 1
1b: n = 3
O
O
O
H
O
H
N
O
O
R = n-C8H17
O
N
O
O
R2N
H
N
H
O
O
4
H2N
NH2
O
O
R = n-C8H17
O
O
O
O
N
H
O
N
H
O
O
O
Fig. 2. Aromatic amide macrocycle precursors 3 and 4.
O
O
N
N
R2N
O
H
H
O
NR2
centered hydrogen bonding, respectively, which should induce
the two appended amino units to point to one side of the back-
bones. The two compounds bear four and two N,N-di(n-octyl)
acetamide side chains, respectively, which were expected to
provide solubility for the resulting rigid macrocycles. 2,3-Dihydro
benzo[b][1,4]dioxine-5,8-diamine was chosen as the diamine
segment not only to expand the cavity of the resulting macro-
cycles, but also to maximize the strength of the hydrogen bonds it
formed by minimize the possible steric hindrance produced by
the ether chains.
O
O
O
O
R2N
NR2
R
O
R
O
O
H
H
N
R
O
N
N
H
N
H
O
O
RO
N
O
R
OR
H
O
O
O
N
H
OR
For the synthesis of 3 (Scheme 1), diamine 524 was first reacted
with (Boc)2O in aqueous THF to afford 6 in 91% yield. Then, amide 7
was prepared from chloroacetyl chloride and di(n-octyl)amine in
40% yield. Treatment of diester 825 with 7 in hot DMF in the pres-
ence of potassium carbonate produced 9 in 93% yield. This diester
was then selectively hydrolyzed into 10 in 49% yield with lithium
hydroxide in aqueous methanol and THF. The acid was then treated
with Ghosez’s reagent (1-chloro-N,N,2-trimethyl-1-propenyl
amine) in dichloromethane to give rise to the corresponding acyl
chloride. Without purification, this intermediate was reacted with 6
in dichloromethane to produce 11 in 99% yield. The ester was fur-
ther hydrolyzed to 12 and the acid was converted into the corre-
sponding acyl chloride under the similar reaction conditions.
Treatment of the acyl chloride with excess of diamine 5 in
dichloromethane afforded 13 in 63% yield.
This intermediate was then treated with trifluoroacetic acid in
dichloromethane to yield 3 quantitatively. With this precursor in
hand, compound 9 was further treated with excess of lithium
hydroxide to produce 14 quantitatively. This diacid was then
reacted with Ghosez’s reagent to give the corresponding diacyl
chloride 15. Treatment of 15 with diamine 3 of the same molar
equivalent in dichloromethane produced the 2þ2 macrocycle 1a
in 72% yield. The mass spectrum of the crude product after
workup did not exhibit the peak of 1þ1, 3þ3 or larger macro-
cycles, suggesting that the folded conformation of the in-
termediates formed from 3 and 15 substantially favored the
formation of 1a over other possible macrocycles. This result also
confirms the stability of the intramolecular hydrogen bonds and
thus the folded conformation of the intermediate for the last cy-
clization step.
2a
N
N
RO
H
R = n-C8H17
H
N
N
O
RO
O
O
N
OR
RO
N
O
H
O
N
H
OR
N
OR
O
N
H
RO
H
O
R
R
R
O
O
O
H
N
H
N
R
O
O
H
N
H
N
R
O
N
O
O
N
O
R
OR
H
H
O
H
RO
N
O
R
O
N
H
OR
O
RO
H
N
N
N
N
O
O
H
O
2b
H
R = n-C8H17
RO
OR
O
RO
RO
N
O
H
H
N
OR
N
N
O
O
H
OR
O
N
RO
N
O
H
O
N
H
OR
N
OR
O
H
For the synthesis of macrocycle 1b (Scheme 1), diacyl chloride
15 was first reacted with diamine 5 to produce 4 in 68% yield.
Further treatment of this diamine with 15 in dichloromethane
produced the 4þ4 macrocycle 1b in 52% yield. Again, the mass
spectrum of the crude product after workup did not exhibit the
peak of other smaller or larger macrocycles, which also illustrated
high cyclization selectivity.
N
H
RO
O
R
Fig. 1. The structures of giant macrocycles 1a, 1b, 2a, and 2b.

Y.-Y. Chen et al. / Tetrahedron 70 (2014) 5483e5487
5485
R
O
R
O
NH2
NH2
NH2
O
O
O
O
O
H
N
H
N
(Boc)2O, THF/H2O (1:2, v/v)
r.t., 24 h, 91%
R
O
N
H
NHBoc
H
O
O
O
RO
N
O
R
NHBoc
6
5
16
O
C8H17
C8H17
Et3N, DMAP, CH2Cl2
0 °C-r.t., 7 h, 40%
Cl
N(C8H17)
2
+
Cl
HN
Cl
R
O
R
O
7
O
O
CHO
H
H
N
R
O
N
LiOH•H2O
THF/MeOH/H2O
7, K2CO3
KI, DMF
O
H
N
N
H
NHBoc
HO
OH
RO
OR
R
O
O
O
N
H
O
R
r.t., 49%
100 °C, 12 h
93%
MeO2C
CO2Me
MeO2C
CO2Me
H
O
O
RO
N
O
R
8
9
17
R = n-C8H17
O
i) Ghosez's reagent,
CH2Cl2, r.t., 2 h
RO
OR
RO
OR
O
H
N
O
MeO2C
ii) 6, DIEA, CH2Cl2,
O
MeO2C
CO2H
O
11
r.t., 0.5 h, 99%
NHBoc
10
i) Ghosez's reagent
CH2Cl2, r.t., 2 h
Fig. 3. Aromatic hydrazide macrocycle precursors 16 and 17.
RO
OR
LiOH•H2O
O
O
H
N
ii) 5, DIEA, CH2Cl2
THF/MeOH/H2O
r.t., 13 h, 86%
HO2C
r.t., 2 h, 63%
O
O
O
NHBoc
HO
RO
12
n-C8H17Br, K2CO3, KI
OMe
OH
OMe
OR
°
O
HN
O
DMF, 80 C, 10 h, 71%
O2N
O2N
OR
RO
NH
18
19
O
TFA, CH2Cl2
RO
OR
NH
RO
3
O
O
KOH, THF/MeOH/H2O
r.t., 4 h, 92%
OH
OR
13
r.t., 24 h
100%
O
HN
O
O
O
O2N
20
O
O
RO
H2NHN
OR
NHNHBoc
BocHN
NHBoc
20, EDCI, HOBt
CH2Cl2, r.t., 14 h, 90%
LiOH•H2O
RO
OR
21
Ghosez's reagent
CH2Cl2, r.t., 1 h
O
O
THF/MeOH/H2O
9
RO
H
N
OR
H
N
r.t., 11 h, 99%
HO2C
CO2H
O
H2, Pd/C, MeOH/THF
r.t., 6 h, 89%
14
RO
N
NHBoc
RO
OR
H
3, DIEA, CH2Cl2
O
O
1a
22
23
O2N
OR
0 °C-r.t., 24 h, 72%
ClOC
15
COCl
OR
RO
OR
H
N
O
H
N
15, DIEA, CH2Cl2
5, DIEA, CH2Cl2
0 °C-r.t., 2 h, 68%
OHC
CO2H
24
RO
1b
N
H
NHBoc
4
0 °C-r.t., 24 h, 52%
ClCO2-i-Bu, NEt3, CHCl3
O
O
H2N
OR
r.t. 72 h, 85%
R = CH2CON(n-C8H17
)
2
Scheme 1. Synthesis of macrocycles 1a and 1b.
TFA, CHCl3
r.t., ultrasonic, 10 h, 98%
16
2a
R = n-C8H17
Scheme 2. Synthesis of macrocycle 2a.
2.2. Synthesis of macrocycles 2a and 2b
We previously reported that hydrogen bonding-induced pre-
organization of aromatic amide or hydrazide precursors that bear
aldehyde and/or amine or monoacylhydrazine units could drive
them to condense into 6-mer macrocycles through the formation of
imine or hydrazone bonds at room temperature in high or nearly
quantitative yield after the reactions reached thermodynamic
equilibrium.16,21 To further expand the scope of this approach, we
also prepared compounds 16 and 17 (Fig. 3) to investigate their self-
condensation to produce shape-persistent macrocycles after the
tert-butoxycarbonyl (Boc) and 2,2-dimethylpropane-1,3-diol pro-
tecting groups were removed with acid. For both compounds, n-
octyl groups were introduced to provide solubility in organic
solvents.
which was activated with iso-butyl chloroformate in chloroform to
generate 16 in 85% yield. Finally, 16 underwent self-coupling in
chloroform under ultrasonic in the presence of TFA to give 2a in 98%
yield. The crude product obtained from the last reaction after
workup did not exhibit the peak of other macrocycles, showing
that, similar to the shorter analogues, the extended conformation of
16 remarkably favored the formation of the 9-mer macrocyclic
structure.
Encouraged by the high yield of 2a formed from 16, we further
prepared the longer precursor 17 that also possesses an extended
conformation (Scheme 3). Thus, compound 19 was first hydroge-
nated to afford 25 quantitatively in methanol, which was catalyzed
by Pd/C. The amine was then coupled with 24, also activated with
iso-butyl chloroformate, to produce 26 in 72% yield. The aldehyde
was then protected by 2,2-dimethyl-1,3-dipropanol in refluxed
toluene in the presence of p-toluenesulfonic acid. The resulting
intermediate 27 was quantitatively hydrolyzed to afford 28 in
aqueous methanol and THF with potassium hydroxide as the base.
With 28 being in hand, compound 30 was prepared in 81% yield
For the synthesis of 16 (Scheme 2), 1826 was first alkylated in
DMF to afford 19 in 71% yield. The ester was then hydrolyzed with
potassium hydroxide in aqueous methanol and THF in 92% yield.
The resulting acid 20 was then coupled with 2127 in dichloro-
methane in the presence of EDCI and HOBt to produce 22 in 90%
yield. Palladium-catalyzed hydrogenation of 22 in methanol and
THF afford 23 in 89% yield. The amine was then coupled with 24,21b

5486
Y.-Y. Chen et al. / Tetrahedron 70 (2014) 5483e5487
O
24, ClCO2-i-Bu
RO
H2, Pd/C, MeOH
r.t., 7 h, 10
NEt3, CHCl3
OMe
OR
19
r.t. 72 h, 72%
H2N
25
RO
CO2Me
OR
RO
CO2Me
OR
OR HN
HO
OH
OR HN
p-TsOH•H2O
O
O
toluene, reflux, 2 h
88%
27
26
O
O
CHO
RO
CO2H
OR
OR HN
KOH
THF/MeOH/H2O
O
60 °C, 4 h, 100%
28
O
O
n-C8H17Br
K2CO3, KI, DMF
HO
CO2Et
OH
RO
EtO2C
CO2Et
OR
80 °C, 8 h, 81%
EtO2C
29
30
RO
EtO2C
CO2H
OR
KOH, THF/EtOH
reflux, 6 h, 64%
21, EDCI, HOBt, CH2Cl2
r.t., 12 h, 62%
31
RO
OR
O
H
H
NH2NH2•H2O, MeOH/THF
60 ºC, 4 h, 91%
RO
N
N
N
NHBoc
H
O
O
32
RO
EtO2C
OR
Fig. 4. Top and side views of the structures of macrocycles (a) 1a, (b) 1b, (c) 2a, and (d)
2b optimized at the M062X/6-31G(d,p) level. For simplicity, all the long side chains are
replaced with methoxyl groups.
OR
H
28, EDCI, HOBt, CH2Cl2
O
H
RO
N
N
N
H
NHBoc
30 °C, 20 h, 70%
H2NHN
O
O
33
OR
O
residue 1a has a conformation resembling a shallow bowl, while
the 16-residue 1b gave rise to a flat backbone, which implies that
the latter’s aromatic backbone has a small ring tension. In contrast,
both 9-residue 2a and 12-residue 2b have a slightly twisted tri-
angular planer conformation, which may be attributed to the
similarity of the extended aromatic backbone of the precursors.
TFA, CHCl3, ultrasonic
r.t., 10 h, 100%
17
2b
R = n-C8H17
Scheme 3. Synthesis of macrocycle 2b.
from the reaction of 2928 with n-octyl bromide in hot DMF in the
presence of potassium carbonate and potassium iodide. Treatment
of 30 with potassium in THF and ethanol under reflux afforded 31 in
64% yield. The acid was then coupled with 21 in dichloromethane in
the presence of EDCI and HOBt to give 32 in 62% yield. The ester was
further reacted with hydrazine in methanol and THF under reflux to
produce 33 in 91% yield. This hydrazine derivative was then cou-
pled with 28 in dichloromethane in the presence of EDCI and HOBt
to afford 17 in 70% yield. In the presence of TFA, the solution of 17
stirred in chloroform under ultrasonic yielded macrocycle 2b in
quantitative yield. The fact that both 2a and 2b were generated
exclusively shows that the dynamic imine chemistry based mac-
rocyclization could occur more selectively because of the feature
that the reactions were of thermodynamic control.
To get more insight into the conformation of the new hydrogen
bonded macrocycles and to estimate the size of their cavity, com-
puter simulations with GAUSSIAN09 program for the model com-
pounds with methoxyl groups were further carried out for all the
four macrocycles. The lowest-energy conformations were opti-
mized with the M062X/6-31G(d,p) calculation method,29 using the
GAUSSIAN09 program. As shown in Fig. 4, all the alkoxyl oxygen
atoms were engaged in intramolecular hydrogen bonding, which
forced the macrocyclic backbone to form a well-defined rigid
conformation. The diameter of the four macrocycles was estimated
to ca. 1.94, 2.75, 1.86, and 2.65 nm, respectively. Notably, the 12-
3. Conclusions
We demonstrate that sizable macrocycles can be prepared from
rationally designed aromatic amide or hydrazide precursors by
making use of strong intramolecular hydrogen bonding to induce
the precursors to adopt preorganized conformation for macro-
cyclization through the formation of 3e8 amide or hydrazone
bonds. The selectivity of both approaches is high, but the yield of
the second approach is much higher and the macrocycles can be
formed quantitatively, which illustrates the robustness of this dy-
namic imine chemistry based macrocyclization strategy. The new
rigid giant aromatic macrocycles have a cavity of nano-scale size.
We are investigating the insertion of the new shape-persistent
macrocycles into lipid membrane and the possibility of trans-
porting large organic molecules.
Acknowledgements
This work was supported by National Natural Science Foun-
dation of China (21172042, 20272042, 91227108, and 21172025),
Technology Commission of Shanghai Municipality (13NM14
00200), Ministry of Education of the People’s Republic of China
(IRT1117) and Ministry of Science and Technology of the People’s
Republic of China (2013CB834501). Y.-Y.C. thanks the Doctoral

Y.-Y. Chen et al. / Tetrahedron 70 (2014) 5483e5487
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