Synthesis, characterisation and fluorescence studies of new bis-phenanthrimidazole derivatives

Article abstract of DOI:10.3184/174751913X13736148050554

The synthesis of new bis-phenanthrimidazole derivatives in one-pot four-component reaction from 9,10-phenanthraquinone, aromatic aldehydes, 4,4'-diaminodiphenyl ether and ammonium acetate is described. These new compounds were subsequently studied for the

Full text of DOI:10.3184/174751913X13736148050554

JOURNAL OF CHEMICAL RESEARCH 2013
RESEARCH PAPER 487
AUGUST, 487–490
Synthesis, characterisation and fluorescence studies of new
bis-phenanthrimidazole derivatives
Seyed Mahdi Saadatia*, Mohammad Hossein Mosslemina, Hossein Behmadib and
Alireza Shamsb
aDepartment of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran
bDepartment of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
The synthesis of new bis-phenanthrimidazole derivatives in one-pot four-component reaction from 9,10-phenanthra-
quinone, aromatic aldehydes, 4,4’-diaminodiphenyl ether and ammonium acetate is described. These new
compounds were subsequently studied for their fluorescence properties.
Keywords: bis-phenanthrimidazoles, 1H-phenanthro[9,10-d]imidazol-2-yl, one-pot reaction, fluorescence, emission and absorption
spectra
The 1H-phenanthro[9,10-d]imidazol-2-yl group is worth con-
sidering as a substituent in the field of molecular materials.1
This group of compounds have also found application as a
chromophore with high extinction coefficients, readily tunable
absorption wavelengths, and fluorophoric properties and are
useful as large planar synthetic building blocks in supramo-
lecular chemistry. Besides early reports2 of its synthesis from
9,10-phenanthraquinone and an aromatic aldehyde, the system
has received little interest.
Fluorescence is a highly sensitive and convenient method of
detection that has significantly influenced the landscape of
molecular biotechnology over the past few decades.An increas-
ingly wide variety of fluorophores is used in biotechnology,
genomics, immunoassays, array technologies, imaging, and
drug discovery.3,4
molecule and infiltration to the cellular regions is readily
accomplished.5,6
Organic fluorophores or fluorescent dyes are characterised
by a strong absorption and emission band in the visible region
of the electromagnetic spectrum. Fluorescent heterocyclic
compounds are of interest as functional materials in many
disciplines such as emitters for electroluminescence devices,7
molecular probes for biochemical research,8 in traditional
textile and polymer fields,9 as whitening agents10 and in
photoconducting materials.11
In the present study, we describe the synthesis of new
bis-phenanthrimidazole derivatives, which have fluorescence
properties, from 9,10-phenanthraquinone, various aromatic
aldehydes, 4,4′-diaminodiphenyl ether and ammonium acetate
in acetic acid (Scheme 1).
Fluorescent molecules can easily be attached to a cast of
target molecules, including DNA, RNA, antibodies, peptides,
and proteins, and have the distinct advantage of being small
compared to several other molecular labels. Fluorescence-
based technologies are used in a wide variety of biotechnology
applications, including automated DNA sequencing, real-time
PCR, microarray analyses, and immunoassays. It has been
shown that the fluorescent dyes which have a small size,
establish little interference with the properties of the labelled
Results and discussion
The new bis-phenanthrimidazole derivatives 4a–k were syn-
thesised via a one-pot four-component reaction from 9,10-
phenanthraquinone, aromatic aldehydes, 4,4′-diaminodiphenyl
ether and ammonium acetate in acetic acid (Scheme 1).
The structures of compounds 4a–k were characterised by
elemental, FTIR, 1H and 13C NMR analyses.
Scheme 1
* Correspondent. E-mail: seyedmahdi_saadati@yahoo.com;
smsaadati@mshdiau.ac.ir

488 JOURNAL OF CHEMICAL RESEARCH 2013
Table 1 Photophysical data for absorption and fluorescence of 4a–k
Compound
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
λabs /nma
260
4.0
260
369
1.24
262
3.0
262
382
0.95
260
2.0
260
393
1.00
260
2.5
260
435
0.80
258
2.5
258
435
0.77
262
3.5
262
384
0.84
261
3.0
261
380
0.89
261
4.0
261
386
1.10
374
3.5
374
392
0.70
361
3.5
366
3.0
366
386
0.80
b
ε × 10−6 /mol−1 L cm−1
λex /nmc
361
λflu/nmd
418
19.35
e
ФF
a Wavelengths of maximum absorbance.
b Extinction coefficient.
c Wavelengths of fluorescence excitation.
d Wavelengths of fluorescence emission.
e Fluorescence quantum yield (%).
In order to study the fluorescence properties of these new
compounds, we investigated the fluorescence absorption
and emission spectra of compounds 4a–k. The λabs, values of
extinction coefficient (ε), λex, λflu and fluorescence quantum
yield (ΦF) data of these compounds are presented in Table 1.
Values of the extinction coefficient (ε) were calculated from
the slope of the plot of absorbance versus concentration. The
fluorescence quantum yields (ΦF) of compounds 4a–k were
determined using comparison methods, with fluorescein as a
standard sample in 0.1 M NaOH and MeOH solution.12 It can
be concluded from the data in Table 1 that these novel com-
pounds are fluorescent. A typical photoinduced charge transfer
system consists of a donor (D) and acceptor (A) couple, which
can be separate chromophores within a large molecule, leading
to intramolecular charge transfer (ICT). Overlap of the imidaz-
ole ring nitrogen with the π-system affords a highly conjugated
array. For example in 4j this occurs from ring-N through to the
acceptor nitrile group centre, as depicted in Scheme 2.
Fig. 1 Visible absorption spectrum of compound 4j in some
solvents (1 × 10−6 mol L−1).
The fluorescence absorption and emission spectra of
compound 4j which had the highest quantum yield (ΦF), were
measured at the concentration of 1 × 10−6 mol L−1 in several
solvents (Figs 1 and 2). As is demonstrated in these figures, the
fluorescence absorption and emission spectra of 4j in polar
solvents exhibited a solvatochromic red shift with increasing
solvent polarity. Solvent effects shift the emission to lower
energy owing to stabilisation of the excited state by the polar
solvent molecules (Table 2). This type of behavior is observed
for most of the dyes. For example, in Table 2, one can see
that in the absorption spectrum for 4j, λabs shifts from 358 to
364 nm, and in the emission spectrum, λflu shifts from 410 to
436 nm as the solvent is changed from n-hexane to methanol.
In conclusion, we have successfully synthesised and charac-
terised new bis-phenanthrimidazole derivatives which have
fluorescence properties; research into their possible applica-
tions is in progress and will be reported elsewhere.
Fig 2 Emission spectrum of compound 4j in some solvents
(1 × 10−6 mol L−1).
Scheme 2

JOURNAL OF CHEMICAL RESEARCH 2013 489
Table 2 Spectroscopic data for 4j at 298 K in dependence of
>350 °C; IR: νmax/cm−1; 3058, 1596, 1574, 1499, 1340, 855; 1H NMR
(400 MHz, CDCl3) δ 7.31 (d, 2H, J = 8.8 Hz), 7.35 (d, 2H, J = 7.2 Hz),
7.44 (d, 4H, J = 8.8 Hz), 7.57 (t, 2H, J = 7.2 Hz), 7.64 (d, 4H, J =
8.8 Hz), 7.70 (t, 2H, J = 7.2 Hz), 7.75–7.82 (m, 6H), 8.12 (d, 4H,
J = 8.8 Hz), 8.71 (d, 2H, J = 8.0 Hz), 8.79 (d, 2H, J = 8.0 Hz), 8.85
(d, 2H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz), δ 120.67, 120.78,
122.68, 122.73, 123.27, 123.53, 124.45, 125.69, 126.27, 126.54,
126.93, 127.65, 128.53, 129.02, 129.78, 129.88, 130.88, 134.09,
136.52, 137.97, 147.51, 148.22, 157.45; MS, m/z: 844. Anal. Calcd
for C54H32N6O5: C, 76.77; H, 3.82; N, 9.95. Found: C, 76.84; H, 3.75;
N, 9.89%.
the solvent
Solvent
λabs/nm
λflu/nm
n-Hexane
Chloroform
Ethyl acetate
Acetone
358
360
360
361
362
362
364
410
420
420
430
433
434
436
DMF
Ethanol
Methanol
1-{4-[4-(2-(2-Nitrophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(2-nitrophenyl)-1H-phenanthro[9,10-d]imidazole
(4e): Dark green powder; reaction time: 50 min; yield: 88%; m.p.
316–318 °C; IR: νmax/cm−1; 3060, 1596, 1570, 1499, 1352, 850;
1H NMR (400 MHz, CDCl3) δ 7.13 (d, 4H, J = 8.8 Hz), 7.31(d, 2H,
J = 8.0 Hz), 7.35 (d, 2H, J = 8.0 Hz), 7.43 (d, 4H, J = 8.8 Hz), 7.55 (d,
2H, J = 7.2 Hz), 7.59 (d, 2H, J = 7.2 Hz), 7.65–7.75 (m, 8H), 8.04 (d,
2H, J = 8.0 Hz), 8.73 (d, 2H, J = 8.4 Hz), 8.76 (d, 2H, J = 8.4 Hz), 8.80
(d, 2H, J = 8.4 Hz); 13C NMR (CDCl3, 100 MHz), δ 119.95, 120.75,
122.72, 122.79, 123.19, 124.32, 124.69, 125.36, 125.89, 126.41,
127.05, 127.50, 127.67, 128.38, 129.54, 130.39, 130.72, 132.70,
133.19, 137.64, 147.79, 148.90, 156.96; MS, m/z: 844. Anal. Calcd
for C54H32N6O5: C, 76.77; H, 3.82; N, 9.95. Found: C, 76.89; H, 3.78;
N, 9.98%.
Experimental
Chemicals were either prepared in our laboratories or purchased from
Merck, Fluka, and Aldrich Chemical Companies. All yields refer to
isolated products. Melting points were recorded on an Electrothermal
type 9100 melting point apparatus. The IR spectrometer used was
Bruker Tensor 27. The IR spectra were taken using KBr pellets. The
1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded
on a Bruker spectrometer. The mass spectra were scanned on a
Varian Mat CH-7 instrument at 70 eV. Absorption and fluorescence
spectra were recorded on a Varian 50-bio UV–Vis spectrophotometer
and a Varian Cary Eclipse spectrofluorophotometer. UV–Vis and
fluorescence scans were recorded from 350 to 700 nm.
1-{4-[4-(2-(4-Chlorophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-chlorophenyl)-1H-phenanthro[9,10-d]imidazole
(4f): Light violet powder; reaction time: 35 min; yield: 90%;
Synthesis of 4a–k; general procedure
1
m.p. 318–320 °C; IR: νmax/cm−1; 3060, 1593, 1497, 848; H NMR
A mixture of an aldehyde (2.0 mmol), 9,10-phenanthraquinone
(2.0 mmol), 4,4′-diaminodiphenyl ether (1.0 mmol) and ammonium
acetate (2.0 mmol) in acetic acid (5 mL) was heated at 120 °C. The
progress of reaction was monitored by TLC. After completion of the
reaction, the mixture was cooled to room temperature. Then the prod-
uct was filtered, washed with water and recrystallised from ethanol to
the following compounds.
1-{4-[4-(2-Phenyl-1H-phenanthro[9,10-d]imidazol-1-yl)phenoxy]-
phenyl}-2-phenyl-1H-phenanthro[9,10-d]imidazole (4a): Light pink
powder; reaction time: 45 min; yield: 90%; m.p. 343–345 °C; IR:
νmax/cm−1; 3070, 1605, 1500, 850; 1H NMR (400 MHz, CDCl3) δ 7.32–
7.35 (m, 14H), 7.51–7.57 (m, 6H), 7.63–7.65 (m, 4H), 7.67 (t, 2H,
J = 7.2 Hz), 7.76 (t, 2H, J = 7.2 Hz), 8.71 (d, 2H, J = 8.4 Hz), 8.79
(d, 2H, J = 8.4 Hz), 8.89 (d, 2H, J = 8.4 Hz); 13C NMR (CDCl3,
100 MHz), δ 120.25, 120.68, 122.80, 123.02, 123.16, 124.29, 125.01,
125.74, 126.34, 127.24, 127.39, 127.85, 128.16, 128.33, 129.02,
129.38, 129.55, 130.53, 130.94, 134.44, 137.51, 151.21, 157.21; MS,
m/z: 754. Anal. Calcd for C54H34N4O: C, 85.92; H, 4.54; N, 7.42.
Found: C, 85.80; H, 4.61; N, 7.35%.
(400 MHz, CDCl3) δ 7.32 (d, 6H, J = 8.8 Hz), 7.37 (d, 6H, J = 8.8 Hz),
7.53 (d, 2H, J = 7.2 Hz), 7.58 (d, 8H, J = 8.8 Hz), 7.67 (t, 2H, J =
7.2 Hz), 7.76 (t, 2H, J = 7.2 Hz), 8.72 (d, 2H, J = 8.0 Hz), 8.79 (d, 2H,
J = 8.0 Hz), 8.85 (d, 2H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz),
δ 120.40, 120.64, 122.73, 122.90, 123.19, 124.34, 125.17, 125.88,
126.39, 127.10, 127.47, 128.34, 128.63, 128.99, 129.48, 130.70,
130.91, 134.29, 135.22, 137.53, 147.50, 149.96, 157.26; MS, m/z:
823. Anal. Calcd for C54H32Cl2N4O: C, 78.73; H, 3.92; N, 6.80. Found:
C, 78.90; H, 3.86; N, 6.93%.
1-{4-[4-(2-(4-Fluorophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-fluorophenyl)-1H-phenanthro[9,10-d]imidazole
(4g): Light violet powder; reaction time: 35 min; yield: 90%; m.p.
>350 °C; IR: νmax/cm−1; 3060, 1596, 1495, 850; 1H NMR (400 MHz,
CDCl3) δ 7.04 (t, 4H, J = 8.8 Hz), 7.30 (d, 4H, J = 8.8 Hz), 7.35 (d,
4H, J = 8.8 Hz), 7.52–7.64 (m, 10H), 7.67 (t, 2H, J = 7.2 Hz), 7.76 (t,
2H, J = 7.2 Hz), 8.72 (d, 2H, J = 8.0 Hz), 8.79 (d, 2H, J = 8.0 Hz), 8.85
(d, 2H, J = 8.0 Hz); 13C NMR (CDCl3, 100 MHz), δ 115.39, 120.33,
120.61, 122.72, 123.18, 124.33, 125.08, 125.82, 126.36, 126.67,
127.12, 127.45, 128.15, 128.31, 129.41, 130.93, 131.45, 131.53,
134.32, 150.26, 157.21, 161.88, 164.36; MS, m/z: 790. Anal. Calcd
for C54H32F2N4O: C, 82.01; H, 4.08; N, 7.08. Found: C, 82.20; H, 4.14;
N, 7.03%.
1-{4-[4-(2-(3,4-Dimethoxyphenyl)-1H-phenanthro[9,10-d]imidazol-
1-yl)phenoxy]phenyl}-2-(3,4-dimethoxyphenyl)-1H-phenanthro-
[9,10-d]imidazole (4h): Dark brown powder; reaction time: 50 min;
yield: 89%; m.p. 198–200 °C; IR: νmax/cm−1; 3066, 1596, 1500, 852;
1H NMR (400 MHz, CDCl3) δ 3.84 (s, 12H, 4CH3), 6.79 (d, 2H,
J = 8.4 Hz), 7.12 (d, 2H, J = 8.4 Hz), 7.31–7.36 (m, 10H), 7.52 (t, 2H,
J = 7.6 Hz), 7.59 (d, 4H, J = 8.4 Hz), 7.66 (t, 2H, J = 7.6 Hz), 7.75 (t,
2H, J = 7.6 Hz), 8.71 (d, 2H, J = 8.4 Hz), 8.78 (d, 2H, J = 8.4 Hz), 8.88
(d, 2H, J = 8.4 Hz); 13C NMR (CDCl3, 100 MHz), δ 55.90, 120.26,
120.57, 122.39, 122.77, 122.98, 123.17, 124.230, 124.91, 125.71,
126.31, 127.13, 127.38, 128.04, 128.27, 129.28, 129.54, 131.05,
134.78, 137.31, 148.63, 149.77, 151.06, 157.19; MS, m/z: 874. Anal.
Calcd for C58H42N4O5: C, 79.62; H, 4.84; N, 6.40. Found: C, 79.70; H,
4.77; N, 6.48%.
1-{4-[4-(2-p-Tolyl-1H-phenanthro[9,10-d]imidazol-1-yl)phenoxy]-
phenyl}-2-p-tolyl-1H-phenanthro[9,10-d]imidazole (4b): Light violet
powder; reaction time: 35 min; yield: 92%; m.p. >350 °C; IR: νmax/cm−1;
1
3065, 1596, 1503, 845; H NMR (400 MHz, CDCl3) δ 2.34 (s, 6H,
2CH3), 7.14 (d, 4H, J = 8.4 Hz), 7.32–7.35 (m, 8H), 7.51–7.58 (m,
10H), 7.66 (t, 2H, J = 7.2 Hz), 7.75 (t, 2H, J = 7.2 Hz), 8.71 (d, 2H,
J = 8.0 Hz), 8.79 (d, 2H, J = 8.0 Hz), 8.88 (d, 2H, J = 8.0 Hz);
13C NMR (CDCl3, 100 MHz), δ 21.39, 120.26, 120.63, 122.79, 123.04,
123.14, 124.28, 124.90, 125.67, 126.30, 127.22, 127.36, 127.60,
128.08, 128.25, 129.06, 129.29, 129.38, 130.48, 130.95, 134.56,
137.45, 151.36, 157.19; MS, m/z: 782. Anal. Calcd for C56H38N4O: C,
85.91; H, 4.89; N, 7.16. Found: C, 85.75; H, 4.73; N, 7.20%.
1-{4-[4-(2-(4-Methoxyphenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-methoxyphenyl)-1H-phenanthro[9,10-d]imidazole
(4c): Light violet powder; reaction time: 35 min; yield: 92%;
m.p. 308–310 °C; IR: νmax/cm−1; 3055, 1590, 1495, 853; H NMR
1
(400 MHz, CDCl3) δ 3.82 (s, 6H, 2CH3), 6.86 (d, 4H, J = 8.4 Hz),
7.32–7.35 (m, 8H), 7.50–7.58 (m, 10H), 7.66 (t, 2H, J = 7.2 Hz), 7.75
(t, 2H, J = 7.2 Hz), 8.71 (d, 2H, J = 8.0 Hz), 8.79 (d, 2H, J = 8.0 Hz),
8.87 (d, 2H, J = 8.0 Hz). 13C NMR (CDCl3, 100 MHz), δ 55.30,
113.79, 120.27, 120.58, 122.76, 122.94, 123.03, 123.14, 124.27,
124.83, 125.63, 126.29, 127.20, 127.33, 127.98, 128.23, 129.23,
130.92, 130.99, 134.62, 137.39, 151.23, 157.18, 160.17; MS, m/z:
814. Anal. Calcd for C56H38N4O3: C, 82.54; H, 4.70; N, 6.88. Found:
C, 82.84; H, 4.65; N, 6.81%.
1-{4-[4-(2-(4-Bromophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-bromophenyl)-1H-phenanthro[9,10-d]imidazole
(4i): Grey powder; reaction time: 45 min; yield: 85%; m.p. >350 °C;
1
IR: νmax/cm−1; 3058, 1600, 1499, 855; H NMR (400 MHz, CDCl3)
δ 7.32–7.58 (m, 16H), 7.61(d, 6H, J = 8.4 Hz), 7.71 (t, 2H, J = 7.2 Hz),
7.78 (t, 2H, J = 7.2 Hz), 8.74 (d, 2H, J = 8.4 Hz), 8.82 (d, 2H, J =
8.4 Hz), 8.90 (d, 2H, J = 8.4 Hz); 13C NMR (CDCl3, 100 MHz),
δ 120.44, 120.66, 122.78, 122.83, 123.19, 123.74, 124.36, 125.30,
126.01, 126.46, 127.55, 128.27, 128.38, 129.53, 130.90, 130.99,
1-{4-[4-(2-(4-Nitrophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-nitrophenyl)-1H-phenanthro[9,10-d]imidazole
(4d): Dark green powder; reaction time: 35 min; yield: 90%; m.p.

490 JOURNAL OF CHEMICAL RESEARCH 2013
131.62, 134.14, 157.28; MS, m/z: 912. Anal. Calcd for C54H32Br2N4O:
C, 71.06; H, 3.53; Br, 17.51; N, 6.14; O, 1.75. Found: C, 71.10; H,
3.58; Br, 17.50; N, 6.10; O, 1.72%.
136.62, 148.03, 156.98; MS, m/z: 892. Anal. Calcd for C54H30Cl4N4O:
C, 72.66; H, 3.39; Cl, 15.89; N, 6.28; O, 1.79. Found: C, 72.73; H,
3.42; Cl, 15.83; N, 6.25; O, 1.77%.
1-{4-[4-(2-(4-Cyanophenyl)-1H-phenanthro[9,10-d]imidazol-1-yl)-
phenoxy]phenyl}-2-(4-cyanophenyl)-1H-phenanthro[9,10-d]imidazole
(4j): Grey powder; reaction time: 25 min; yield: 88%; m.p. >350 °C;
IR: νmax/cm−1; 3058, 2223, 1606, 1498, 1238, 844; 1H NMR (400 MHz,
CDCl3) δ 7.34 (d, 2H, J = 8.4 Hz), 7.38 (t, 2H, J = 7.2 Hz), 7.45
(d, 4H, J = 8.4 Hz), 7.60 (t, 2H, J = 7.2 Hz), 7.64–7.68 (m, 8H), 7.73
(t, 2H, J = 7.2 Hz), 7.78–7.83 (m, 6H), 8.74 (d, 2H, J = 8.4 Hz),
8.82 (d, 2H, J = 8.4 Hz), 8.90 (d, 2H, J = 8.4 Hz); 13C NMR (CDCl3,
100 MHz), δ 112.53, 118.40, 120.63, 120.75, 122.60, 122.86, 123.26,
124.47, 125.72, 126.36, 126.57, 127.72, 128.53, 128.75, 129.76,
130.87, 132.10, 133.91, 148.44, 157.43; MS, m/z: 805. Anal. Calcd
for C56H32N6O: C, 83.56; H, 4.01; N, 10.44; O, 1.99. Found: C, 83.48;
H, 4.05; N, 10.42; O, 2.05%.
Received 28 March 2013; accepted 9 June 2013
Paper 1301864 doi: 10.3184/174751913X13736148050554
Published online: 9 August 2013
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1-yl)phenoxy)phenyl)-2-(2,4-dichlorophenyl)-1H-phenanthro[9,10-d]-
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1
87%; m.p. 218–220 °C; IR: νmax/cm−1; 3062, 1600, 1502, 1243; H
7
8
9
NMR (400 MHz, CDCl3) δ 7.20 (d, 4H, J = 8.4 Hz), 7.32–7.49 (m,
10H), 7.52 (d, 4H, J = 8.4 Hz), 7.60 (t, 2H, J = 7.2 Hz), 7.70 (t, 2H,
J = 7.2 Hz), 7.77 (t, 2H, J = 7.2 Hz), 8.75 (d, 2H, J = 8.4 Hz), 8.85
(t, 4H, J = 9.2 Hz); 13C NMR (CDCl3, 100 MHz), δ 119.80, 120.78,
122.62, 122.85, 123.20, 124.33, 125.47, 126.03, 126.47, 126.95,
127.37, 127.61, 128.38, 128.70, 129.58, 130.14, 133.57, 135.97,
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