Towards hybrid carbazole/pyrrole-based carboxylated monomers: Chemical synthesis, characterisation and electro-oxidation properties

Article abstract of DOI:10.1016/j.tetlet.2011.10.047

Six novel hybrid carbazole (Cbz)-pyrrole (Pyr)-based carboxylated monomers were synthesised and unambiguously characterised using common spectroscopic tools. Clauson-Kaas, amide coupling, LAH (lithium aluminium hydride)-mediated reduction, esterification

Full text of DOI:10.1016/j.tetlet.2011.10.047

Tetrahedron Letters 52 (2011) 6903–6907
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Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Towards hybrid carbazole/pyrrole-based carboxylated monomers: chemical
synthesis, characterisation and electro-oxidation properties
Jean-Paul Lellouche a, , Zvika Pomerantz a, Subrata Ghosh a,b,
⇑
⇑
a Department of Chemistry, Nanomaterials Research Center, Institute for Nanotechnology and Advanced Materials, Bar-Ilan University, Ramat-Gan 52900, Israel
b School of Basic Sciences, Indian Institute of Technology Mandi, Mandi 175001, India
a r t i c l e i n f o
a b s t r a c t
Article history:
Six novel hybrid carbazole (Cbz)–pyrrole (Pyr)-based carboxylated monomers were synthesised and
unambiguously characterised using common spectroscopic tools. Clauson-Kaas, amide coupling, LAH
(lithium aluminium hydride)-mediated reduction, esterification and debenzylation reactions were used
as key chemical reactions towards their multi-step synthesis. The electro-oxidation features of all these
six hybrid Cbz/Pyr-monomers were investigated for the electro-deposition of corresponding polyCOOH
conducting coatings. Quite interestingly, and due to the fact that such electro-oxidisable monomers con-
tain both types of oxidisable heterocycles, that is, Pyr and Cbz species, it was found that the successful
electro-polymerisation of these hybrid Cbz/Pyr-monomers was highly dependent on the relative number
of Cbz versus Pyr unit(s) present in corresponding monomers. Indeed, a successful electro-deposition of
the corresponding conducting polymeric films onto a working Pt electrode was observed only for hybrid
monomers characterised by a Cbz/Pyr unit(s) ratio greater than or equal to 1. This result has been vali-
dated by systematically tuning the number of oxidisable Cbz and Pyr unit(s) present in monomers
through proper chemical design and monomer multi-step synthesis. In that case, cyclic voltammogram
analyses readily confirmed the exclusive electro-deposition of conducting polyCbz-films.
Received 29 August 2011
Revised 7 October 2011
Accepted 9 October 2011
Available online 14 October 2011
Keywords:
Polycarbazole
Polypyrrole
Hybrid monomers
Electro-polymerisation
Conducting polymers
Ó 2011 Elsevier Ltd. All rights reserved.
Electro-polymerisation of carbazole (Cbz) and pyrrole (Pyr) het-
erocycles is an important chemico-technological tool for the fabrica-
tion of corresponding conducting polymer (CP)-modified electrodes
as they find wide applications in various fields such as chemical
sensing, photoconductive materials, light-emitting diodes, electro-
chromic materials, etc.1–19 Furthermore, functionalised CP films
are of special interest because of their potential applications in the
biosensing field.20–25 Over the years, various Cbz- and Pyr-based
functional and non-functional oxidisable monomers have been devel-
oped through proper chemical design, and their electro-polymerisa-
tion towards corresponding conductive coatings has been studied
extensively.26–30 To investigate their mechanism of formation/
growth and to understand the potential effect of various added
chemical species, such electro-polymerisation processes of Cbz-
and Pyr-monomers were studied under different experimental con-
ditions,31–33 including different solvents and in the presence of some
other added interfering chemical entities such as perchloric acid,4
water,32 hydrochloric acid,34 surfactants,35 pyridine,36 etc. In addi-
tion, it is a well-established fact that the electro-polymerisation of
shortN-hydroxyalkyl orN-carboxyalkyl chain-basedPyr-monomers
is blocked due to intramolecular trapping of in situ-generated cation
radicals by close nucleophilic hydroxyl or acidic hydroxyl
groups.37,38 On the other hand, electrochemical copolymerisation
of Pyr- and Cbz-species in the presence of other polymerisable enti-
ties such as aniline, furan, styrene, terthiophene, etc. is also a well-
studied area of research. Indeed, it enables the easy fabrication of
hybrid functional polymers with modified physical properties.39–45
For example, in order to tailor the surface properties of electro-poly-
merised conductive films, several hybrid oxidisable monomers
based on carbocycle- or heterocycle-attached/fused Cbz- or Pyr-
based monomers have been prepared and their electro-oxidation
behaviour has been intensively investigated.6,46–50 Despite numer-
ous efforts invested in this field, to the best of our knowledge, there
isnoexistingreportdealingwiththesynthesisandelectro-oxidation
properties of hybrid Cbz/-Pyr-based carboxylated monomers.
In the present study, we report our own strategy for the
incremental synthesis of new and different Cbz/Pyr-based hybrid
monomers followed by an investigation into their respective
electro-oxidation properties. In order to rationally investigate the
electro-polymerisation behaviour of such hybrid Cbz/Pyr-based
monomers, the relative ratios of Cbz versus Pyr unit(s) in each
monomer were changed systematically through proper chemical
design and monomer multi-step synthesis.
⇑
Corresponding authors. Tel.: +972 3 531 8324; fax: +972 3 738 4053 (J.-P.L.);
tel.: +91 1905 237926; fax: +91 1905 237924 (S.G.).
To begin our investigation strategy, we initially synthesised two
carboxylated hybrid monomers 7 and 8 (Scheme 1). The basic
E-mail addresses: lellouj@biu.ac.il (J.-P. Lellouche), subrata@iitmandi.ac.in,
sghoshchem2002@iitmandi.ac.in (S. Ghosh).
0040-4039/$ - see front matter Ó 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tetlet.2011.10.047

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J.-P. Lellouche et al. / Tetrahedron Letters 52 (2011) 6903–6907
difference between these two monomers is the presence of differ-
ent numbers of Cbz and Pyr unit(s). Monomer 7 contains one Pyr
unit (Pyr1) and two Cbz units (Cbz2), whereas monomer 8 contains
one Cbz unit and two Pyr units. The synthetic procedures used for
the preparation of these specific monomers are outlined in
Scheme 1. The starting C2-symmetrical amino building blocks 1
and 2 were synthesised following a literature procedure.37 All
other Cbz- and Pyr-based building blocks 3, 4, 9, 13, 16, 17 and
20 were synthesised by a modified Clauson-Kaas ring closure reac-
tion37,51–55 using 2,5-dimethoxy-tetrahydrofuran (DMT) and corre-
sponding amino acid derivatives as the key starting materials
(amino acid, DMT, NaOAC, AcOH, H2O, 75 °C, 2 h, 42–76% yields
for 3, 13 and 17; amino acid, DMT, dioxane, AcOH, HCl, reflux for
3 h and then overnight stirring at rt, 27–30% yields for 4, 9, 16
and 20). The amidation of the amino building blocks 1 and 2 with
the carboxyl building blocks 3 and 4 used a combination of dicyclo-
hexyl-carbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) and tri-
ethylamine (TEA) as efficient coupling systems affording the
bonate–dimethylcarbonate solution as the background electrolyte;
details are available in the following sections), the monomer Pyr1/
Cbz2-7 successfully produced a conducting polymeric poly(Pyr1/
Cbz2-7) film on a Pt electrode, but no polymeric film was formed
when testing the monomer Pyr2/Cbz1-8. Interestingly, this experi-
mental result likely indicates that, in the case of hybrid carboxyl-
ated Cbz/Pyr-based monomers, their electro-polymerisation may
entirely depend on the relative number of Cbz and Pyr unit(s) pres-
ent in their basic structures. To gain more evidence to support this
conclusion, we next synthesised the monomer Pyr2/Cbz2-11, which
contains an equal number of Cbz and Pyr units (two Cbz and two
Pyr units). The monomer Pyr2/Cbz2-11 was also synthesised by
coupling both amino building block 2 and dicarbazole-based build-
ing block 9, yielding the intermediate 10 (61%), followed by deben-
zylation (Scheme 1, 75% yield for Pyr2/Cbz2-11).
The electro-polymerisation of monomer Pyr2/Cbz2-11 was
tested under similar conditions as those stated above, and resulted
in the formation of a stable polymeric conducting film on the Pt
working electrode. Consequently, to know the fate of a hybrid
Cbz/Pyr-monomer containing one unit of Cbz and Pyr each, we syn-
thesised the monomer Pyr1/Cbz1-15 (Scheme 1). The starting Cbz-
based amino building block 12 was synthesised in two steps fol-
lowing a reported procedure.55 The coupling of 12 with the carbox-
ylated Pyr-based building block 13 in the presence of DCC and
HOBt produced the intermediate 14 (78%), which upon debenzyla-
tion yielded the desired hybrid monomer Pyr1/Cbz1-15 (88% yield
for 15). Monomer 15, upon oxidative electro-polymerisation,
corresponding amidated intermediates
5 (67%) and 6 (64%),
respectively. The desired carboxylated hybrid monomers Pyr1/
Cbz2-7 and Pyr2/Cbz1-8 were synthesised by straightforward deb-
enzylation of intermediates 5 and 6, respectively (H2 gas in the
presence of a catalytic amount of 10% Pd/C, 80% yields). Next, we
investigated the electro-oxidation behaviour of Pyr1/Cbz2-7 and
Pyr2/Cbz1-8. Interestingly, we observed that upon electro-polymer-
isation (cyclic voltammetry at 50 mV/sec, three electrode-cell, a
mixture of 0.2 M n-Bu4NClO4 and 0.2 M LiClO4 in a ethylenecar-
N
NH2
N
N
MeOOC
O
O
12
O
N
N
N
N
N
H
H
11
N
COOH
COOH
HOOC
COOH
2. H2, Pd-C, THF,
iPrOH, rt. (88%)
BnO2C
13
1. DCC, HOBt, CH2Cl2,
rt. (78%) (14)
N
N
2. H2, Pd-C, THF,
iPrOH, rt, (75%)
N
COOH
9
1.DCC, HOBt, Et3N, CH2Cl2, rt
N
(61%) (10)
MeOOC
N
O
H
15
O
O
H
N
N
N
H
N
N
H
CO2Bn
CO2Bn
Cbz-based (1)
Pyr-based (2)
N
1.DCC, HOBt, Et3N, CH2Cl2, rt
(64%) (6)
2. H2, Pd-C, THF, iPrOH, rt
(80%)
N
1.DCC, HOBt, Et3N, CH2Cl2, rt
(67%) (5)
2. H2, Pd-C, THF, iPrOH, rt
(80%)
HOOC
HOOC
4
3
N
N
O
O
O
O
O
O
N
N
N
N
N
N
N
N
N
N
H
H
H
H
COOH
COOH
COOH
COOH
7
8
Scheme 1. Synthesis of hybrid carboxylated Cbz/Pyr-based monomers with a Cbz/Pyr ratio of 1:2, 2:1 and 1:1.

J.-P. Lellouche et al. / Tetrahedron Letters 52 (2011) 6903–6907
6905
successfully produced a stable conductive poly(Pyr1/Cbz1-15) film.
From the electro-polymerisation results of these four carboxylated
hybrid Cbz/Pyr-monomers Pyr1/Cbz2-7, Pyr2/Cbz1-8, Pyr2/Cbz2-11
and Pyr1/Cbz1-15, one can readily conclude that successful elec-
tro-polymerisation/conducting film growth can be expected only
for carboxylated hybrid Cbz/Pyr-monomers for which the Cbz to
Pyr unit(s) ratio is greater than or equal to 1. Finally, and in order
to reinforce such an attractive conclusion, we decided to synthesise
one additional pair of hybrid Cbz/Pyr-monomers containing differ-
ent and higher numbers of Cbz and Pyr units. For this purpose, we
synthesised monomers Pyr3/Cbz2-27 and Pyr2/Cbz3-28 following
the reaction procedures outlined in Scheme 2. Both starting diCbz-
and diPyr-based esters 16 and 17 were synthesised from the read-
25 and 26 (46% and 42% yields). Finally, the debenzylation of 25
and 26 yielded the final targeted dicarboxylated hybrid monomers
Pyr3/Cbz2-27 and Pyr2/Cbz3-28 (76% and 75% yields). Monomer 27
contains three Pyr and two Cbz units, whereas monomer 28 con-
tains three Cbz and two Pyr units. Next, and quite similarly, we
investigated the electro-oxidation behaviour of both compounds
Pyr3/Cbz2-27 and Pyr2/Cbz3-28. The electro-polymerisation results
fully agreed with our previously drawn conclusion. While mono-
mer Cbz3/Pyr2-28 with a Cbz/Pyr ratio >1 produced a stable con-
ductive film upon electro-polymerisation, no such film was
formed upon electro-polymerisation of monomer Cbz2/Pyr3-27
which possesses a Cbz/Pyr ratio <1.
The final carboxylated hybrid monomers were foamy in nature.
No column purification was necessary in the final debenzylation
step since a simple washing of the crude products with suitable
solvents (see Supplementary data section for details) yielded spec-
troscopic grade final products. Common spectroscopic tools such
as 1H/13C NMR (300 and 75 MHz, respectively), mass spectrometry
analyses, etc. were used for the unambiguous characterisation of
all intermediates and final compounds.
ily available (commercial source) material L-lysine methyl ester
using a modified Clauson-Kaas ring closure reaction.37,51–55 The
LiAlH4-mediated reduction of these esters produced the corre-
sponding alcohols 18 and 19 (95% and 96% yields, respectively)
which on further esterification with Cbz and Pyr-based building
blocks (S)-20/13 in the presence of a combination of DCC and
dimethylaminopyridine (DMAP) produced both intermediates 21
and 22 (82% and 77% yields). The building blocks 13 and 20 were
The electrochemical studies dealing with this entire set of
potentially oxidisable hybrid Cbz/Pyr-molecules consisted of two
discrete steps. The first step dealt with the tentative electro-poly-
merisation of hybrid Cbz/Pyr-based monomers previously synthes-
ised on a Pt working electrode. In the second step, the resulting
modified electrodes were washed intensively using CH3CN and
were immersed in a monomer-free electrolyte solution (a mixture
of 0.2 M n-Bu4NClO4 and 0.2 M LiClO4 in an ethylenecarbonate–
similarly synthesised from a protected L-glutamic acid derivative
(benzylated H-Glu-Z) according to known procedures.37,55 A cata-
lytic amount of 10% Pd/C was used as the debenzylating catalytic
agent to convert ester intermediates 21 and 22 to the correspond-
ing acid intermediates 23 and 24 (91% and 90% yields, respec-
tively), which on further amidation with C2-symmetrical
building blocks 1 and 2 produced the final amide intermediates
Cbz-based (18)
Pyr-based (19)
°
LAH, Et2O, 0 C
N
N
N
N
(95-96%)
HO
MeOOC
Cbz-based (16)
Pyr-based (17)
1. DMAP, DCC, CH2Cl2, rt
(77-82%) Cbz-based (21)
Pyr-based (22)
Cbz-based (20)
Pyr-based (13)
N
BnO2C
COOH
2. H2, Pd-C, THF, iPrOH,
rt (90-91%)
N
N
N
O
HOOC
O
1. 2, DCC, HOBt, Et3N, CH2Cl2, rt
(42%) (26)
Cbz-based (23)
Pyr-based (24)
1. 1, DCC, HOBt, Et3N, CH2Cl2, rt
(46%) (25)
2. H2, Pd-C, THF, iPrOH, rt
(75%)
2. H2, Pd-C, THF, iPrOH, rt
(76%)
N
N
N
O
N
O
O
O
N
N
O
O
O
O
O
O
N
N
N
N
N
N
N
N
N
N
H
H
H
H
28
COOH
COOH
COOH
COOH
27
Scheme 2. Synthesis of higher order carboxylated hybrids Cbz/Pyr-based monomers with a Cbz/Pyr ratio of 2:3 and 3:2, respectively.

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J.-P. Lellouche et al. / Tetrahedron Letters 52 (2011) 6903–6907
Figure 1. (a) Oxidative electro-polymerisation of hybrid monomer Pyr1/Cbz2-7. (b) Cyclic voltammogram of the resulting conducting poly(Pyr1/Cbz2-7) film.
Table 1
Summary of electro-polymerisation results for all hybrid monomers
Monomers
Cbz unit(s)
Pyr unit(s)
Cbz/Pyr ratio
Polymerisation result
Pyr window Cbz window
7
8
11
15
27
28
2
1
2
1
2
3
1
2
2
1
3
2
>1
<1
1
1
<1
>1
Negative
Positive
Negative
Positive
’’
Negative
Positive
’’
’’
’’
’’
’’
dimethylcarbonate solution (1:2 molar ratio)) to study the voltam-
metric responses of the resulting conducting films.
appeared on the first scan. Moreover, the current of the first peak
increased much faster from one scan to another than the current
of the second peak. These differences rather emphasized the fact
that these two observed peaks arose from different electrochemi-
cal processes: oxidation of the deposited polymer (at ca. 0.6 V)
and oxidation of the monomers to produce the polymer (at ca.
0.9 V).56,57 The film characterisation in monomer-free solutions
(typical CV, Fig. 1b) strongly resembled the polymerisation voltam-
mograms. This assay showed one broad peak appearing at ca. 0.9 V
reflecting the polymer insulator to conductor transformation via a
well-known polaron–bipolaron mechanism.57,59
Quite interestingly, not all the hybrid Cbz/Pyr-monomers pre-
sented the same response during the electro-polymerisation pro-
cesses according to tested Cbz/Pyr-electro-oxidation windows.
When the hybrid monomers Pyr1/Cbz2-7, Pyr2/Cbz1-8, Pyr2/Cbz2-
11, Pyr1/Cbz1-15, Pyr3/Cbz2-27 and Pyr2/Cbz3-28 were subjected
to electro-polymerisation individually under a wide electrochemi-
cal window covering both the Cbz and Pyr-heterocycle oxidation
potential ranges (i.e., À1.0 to 1.1 V), we did not observe any
copolymerisation of Pyr and Cbz species in any of the hybrid
monomers. The electro-polymerisation features of all Cbz/Pyr-
based hybrid monomers are summarised in Table 1.
In conclusion, we have synthesised six novel carboxylated hy-
brid Cbz/Pyr-based monomers in which the number of Cbz and
Pyr unit(s) in each monomer has been tuned systematically for
testing their electro-chemical behaviours. All these monomers
have been characterised spectroscopically. When these monomers
were subjected to electro-polymerisation, we observed that the
monomer(s) containing a Cbz-unit/Pyr-unit ratio P1 successfully
produced electro-conductive film(s) on a working Pt electrode.
Although the mechanism is not clear to us, it seems that
nucleophilic Pyr has a terminating effect on the growth of the
Accordingly, the electro-polymerisation of all hybrid Cbz/Pyr-
monomers was investigated by cyclic voltammetry (50 mV/sec)
on a 1 mm diameter Pt working electrode using a three-electrode
cell (Pt ribbon counter-electrode, Ag/AgNO3 reference electrode)
operated 10 times between 0 and 1.1 V (for Cbz polymerisations),
À1.0 and 0.8 V (for Pyr polymerisations), or between À1.0 and
1.1 V for potential copolymerisations. The background electrolyte
consisted of a mixture of 0.2 M n-Bu4NClO4 and 0.2 M LiClO4 in
an ethylenecarbonate–dimethylcarbonate solution (1:2 molar ra-
tio) in which the monomer concentrations were adjusted to
5 mM. All the electrochemistry experiments were performed under
a glove box atmosphere (dry Ar containing less than, 1 ppm H2O
and O2).
An illustrative cyclic voltammogram of the electro-polymerisa-
tion process of monomer Pyr1/Cbz2-7 and its typical electrochem-
ical behaviour are reported above in Figure 1. The observed current
increase during polymerisation process testing from one scan to
another indicates the successful growth of a conducting polymer
phase. The subsequent voltammogram analysis was mainly based
on previous conclusions relating to (i) the electro-polymerisation
of a typical dicarbazole-based monomer (namely 2,6-bis-carba-
zole-9-yl-hexanoic acid pentafluorophenyl ester)56,57 and to (ii)
the electro-chemical characterisation of the corresponding poly-
DiCbz-polymer. In brief, we noted two main peaks in the polymer-
isation voltammogram appearing at ca. 0.6 V and at ca. 0.9 V. The
first peak may be assigned to the oxidation of the deposited con-
ducting polymer (doping process) and the latter to the oxidation
of hybrid Cbz/Pyr-monomers to produce the corresponding con-
ducting polymers.56,58 We noticed that the lower potential peak
appeared only on the second scan, while the higher potential peak

J.-P. Lellouche et al. / Tetrahedron Letters 52 (2011) 6903–6907
6907
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of the resulting conducting films in supporting electrolyte (without
monomer) and scanned copies of 1H NMR and 13C NMR spectra of
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