Communication
ChemComm
J- or H-aggregation is not related to the outcome of the fluores-
cence. The fluorescence on and off behaviour is dependent on
what type of the solvent is chosen (aromatic or aliphatic).
FT-IR studies (Fig. S9, ESI†) showed that the N–H stretching
J.-P. Desvergne, J. Mater. Chem. C, 2013, 1, 3305; (e) B. O. Okesola and
D. K. Smith, Chem. Commun., 2013, 49, 11164; ( f ) J. R. Moffat and
D. K. Smith, Chem. Commun., 2011, 47, 11864; (g) J. Raeburn,
A. Z. Cardoso and D. J. Adams, Chem. Soc. Rev., 2013, 42, 5143;
(h) K. Liu and J. W. Steed, Soft Matter, 2013, 9, 11699; (i) J. A. Foster,
D. W. Johnson, M.-O. M. Pipenbrock and J. W. Steed, New J. Chem.,
ꢀ
1
band in the non-gel solution state appeared at 3400 cm and it
2014, 38, 927; ( j) N. Yan, Z. Xu, K. K. Diehn, S. R. Raghavan, Y. Fang
ꢀ1
was shifted to 3285 cm in the octane gel. This indicates the
involvement of hydrogen bonds in gel formation. In the case of
and R. G. Weiss, J. Am. Chem. Soc., 2013, 135, 8989; (k) S. S. Babu,
V. K. Praveen and A. Ajayaghosh, Chem. Rev., 2014, 114, 1973.
2 (a) S. S. Babu, S. Prasanthkumar and A. Ajayaghosh, Angew. Chem.,
Int. Ed., 2012, 51, 1766; (b) A. Ajayaghosh, V. K. Praveen and
C. Vijayakumar, Chem. Soc. Rev., 2008, 37, 109; (c) D. J. Cornwell,
B. O. Okesola and D. K. Smith, Soft Matter, 2013, 9, 8730;
ꢀ
1
ꢀ1
toluene gel, two peaks at 3400 cm
and 3285 cm
were
observed. The latter corresponds to the hydrogen bonded
N–H stretching frequency, while the former is attributed to
the non-hydrogen bonded N–H stretching frequency. The
simultaneous observation of these two peaks suggests the
(
2
d) S. Basak, J. Nanda and A. Banerjee, J. Mater. Chem., 2012,
2, 11658; (e) S. Basak, J. Nanda and A. Banerjee, Chem. Commun.,
2
014, 50, 2356; ( f ) A. Baral, S. Roy, A. Dehsorkhi, I. W. Hamley,
3
a,12
formation of a CT complex in the toluene gel.
S. Mohapatra, S. Ghosh and A. Banerjee, Langmuir, 2014, 30, 929.
(a) P. Mukhopadhyay, Y. Iwashita, M. Shirakawa, S.-i. Kawano,
N. Fujita and S. Shinkai, Angew. Chem., Int. Ed., 2006, 45, 1592;
3
X-ray diffraction studies of xerogels were carried out to
obtain the structural insight into the assembled gel state of
compound 1. X-ray diffraction (XRD) patterns of xerogels
obtained from n-octane and toluene are shown in the Fig. S10
(
b) H. Shao, J. Seifert, N. C. Romano, M. Gao, J. J. Helmus,
C. P. Jaroniec, D. A. Modarelli and J. R. Parquette, Angew. Chem.,
Int. Ed., 2010, 49, 7688; (c) H. Shao and J. R. Parquette, Chem.
Commun., 2010, 46, 4285; (d) S. K. M. Nalluri, C. Berdugo, N. Javid,
P. W. J. M. Frederix and R. V. Ulijn, Angew. Chem., Int. Ed., 2014,
(ESI†). Similar XRD patterns were observed for these two gels.
In a low angle region (Fig. S10a, ESI†) two peaks appeared at
53, 5882.
2
4
y = 2.021 and 3.571 corresponding to the d spacing values of
3.4 Å and 24.6 Å, respectively, for the n-octane gel. Similarly,
4 (a) F. B. L. Cougnon, N. Ponnuswamy, N. A. Jenkins, G. D. Pantos- and
J. K. M. Sanders, J. Am. Chem. Soc., 2012, 134, 19129; (b) F. B. L.
Cougnon, H. Y. A-Yeung, G. D. Pantos- and J. K. M. Sanders, J. Am.
Chem. Soc., 2011, 133, 3198; (c) H.-P. J. de Rouville, J. Iehl, C. J. Bruns,
P. L. McGrier, M. Frasconi, A. A. Sarjeant and J. F. Stoddart, Org. Lett.,
for the toluene gel two peaks appeared at 2y = 1.951 and 3.501
corresponding to the d spacing values of 45.0 Å and 25.0 Å,
respectively. In both cases, the first peak observed at 43.4 Å for
the n-octane gel and 45.0 Å for the toluene gel nearly matches
with the molecular length with compound 1. Periodic peaks
were also noticed at 24.6 Å (d/2) and 12.24 Å (d/3) for the
n-octane gel and at 25.0 Å (d/2) and 13.9 Å (d/3) for the toluene
gel, respectively (Fig. S10b and c, ESI†). These ordered peaks are
suggestive of the lamellar packing in the gel state.
In summary, a NDI-based new gelator molecule was
designed and synthesised. It forms gels in various aromatic
as well as aliphatic solvents. Interestingly, compound 1 exhibits
solvent dependent fluorescence ‘on and off’ behaviour as well
as the J- or H-type of aggregation has been controlled depending
on the proper choice of the solvent system whether it is aromatic
or aliphatic. Moreover, it shows a fascinating example of tuning
fluorescence emission from cyan to yellow by varying the
aromatic solvent from benzene to mesitylene with different
electron donating capacity that can interact with the NDI core.
This holds future promise for making n-type semiconducting
NDI-based new soft materials with fascinating properties.
S.B., N.N. and A.B. acknowledge CSIR and DST for financial
assistance.
2012, 14, 5188; (d) K. Tambara, J.-C. Olsen, D. E. Hansen and
G. D. Pantos-, Org. Biomol. Chem., 2014, 12, 607.
5
(a) R. S. K. Kishore, O. Kel, N. Banerji, D. Emery, G. Bollot, J. Mareda,
A. G-Casado, P. Jonkheijm, J. Huskens, P. Maroni, M. Borkovec,
E. Vauthey, N. Sakai and S. Matile, J. Am. Chem. Soc., 2009,
131, 11106; (b) J. Raeburn, T. O. McDonald and D. J. Adams, Chem.
Commun., 2012, 48, 9355.
6 N. B. Kolhe, R. N. Devi, S. P. Senanayak, B. Jancy, K. S. Narayan and
S. K. Asha, J. Mater. Chem., 2012, 22, 15235.
7
(a) M. Kumar and S. J. George, Nanoscale, 2011, 3, 2130; (b) T. D. M. Bell,
S. V. Bhosale, C. M. Forsyth, D. Hayne, K. P. Ghiggino, J. A. Hutchison,
C. H. Jani, S. J. Langford, M. A.-P. Lee and C. P. Woodward, Chem.
Commun., 2010, 46, 4881; (c) S. Basak, J. Nanda and A. Banerjee, Chem.
Commun., 2013, 49, 6891; (d) M. Kumar and S. J. George, Chem. – Eur. J.,
2011, 17, 11102.
8 (a) F. W u¨ rthner, T. E. Kaiser and C. R. S-M ¨o ller, Angew. Chem., Int.
Ed., 2011, 50, 3376; (b) S. Ghosh, X.-Q. Li, V. Stepanenko and
F. W u¨ rthner, Chem. – Eur. J., 2008, 14, 11343; (c) S. Yagai, T. Seki,
T. Karatsu, A. Kitamura and F. W u¨ rthner, Angew. Chem., Int. Ed.,
2008, 47, 3367; (d) S. Gadde, E. K. Batchelor, J. P. Weiss, Y. Ling and
A. E. Kaifer, J. Am. Chem. Soc., 2008, 130, 17114.
9
(a) S. V. Bhosale, C. H. Jani and S. J. Langford, Chem. Soc. Rev., 2008,
7, 331; (b) T. Weil, T. Vosch, J. Hofkens, K. Peneva and K. M u¨ llen,
Angew. Chem., Int. Ed., 2010, 49, 9068.
3
10 (a) S. V. Bhosale, S. V. Bhosale and S. K. Bhargava, Org. Biomol.
Chem., 2012, 10, 6455; (b) N. Sakai, J. Mareda, E. Vauthey and
S. Matile, Chem. Commun., 2010, 46, 4225.
1
1 (a) B.-K. An, D.-S. Lee, J.-S. Lee, Y.-S. Park, H.-S. Song and S. Y. Park,
J. Am. Chem. Soc., 2004, 126, 10232; (b) S. Datta and S. Bhattacharya,
Chem. Commun., 2012, 48, 877; (c) J. W. Chung, B.-K. An and
S. Y. Park, Chem. Mater., 2008, 20, 6750; (d) Y. Hong, J. W. Y. Lam
and B. Z. Tang, Chem. Soc. Rev., 2011, 40, 5361.
Notes and references
1
(a) V. Castelletto, R. J. Gouveia, C. J. Connon, I. W. Hamley,
J. Seitsonen, J. Ruokolainen, E. Longo and G. Siligardi, Biomater. 12 S. Basak, S. Bhattacharya, A. Datta and A. Banerjee, Chem. – Eur. J.,
Sci., 2014, 2, 867; (b) J. K. Sahoo, S. K. M. Nalluri, N. Javid, H. Webb
2014, 20, 5721.
and R. V. Ulijn, Chem. Commun., 2014, 50, 5462; (c) S. Fleming, 13 (a) Y. Zhang, D. Li, Y. Li and J. Yu, Chem. Sci., 2014, 5, 2710;
S. Debnath, P. W. J. M. Frederix, T. Tuttle and R. V. Ulijn, Chem.
Commun., 2013, 49, 10587; (d) S. Banerjee, R. K. Das, P. Terech, A. de
Geyer, C. Aymonier, A. L. Serani, G. Raffy, U. Maitra, A. D. Guerzo and
(b) Z.-H. Guo, Z.-X. Jin, J.-Y. Wang and J. Pei, Chem. Commun., 2014,
50, 6088; (c) D. D. Prabhu, A. P. Sivadas and S. Das, J. Mater. Chem. C,
2014, 2, 7039.
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