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. 2019 Dec 19;9(72):42219-42227.
doi: 10.1039/c9ra08033c. eCollection 2019 Dec 18.

Insights into a novel class of azobenzenes incorporating 4,6- O-protected sugars as photo-responsive organogelators

P V Bhavya  1 , V Rabecca Jenifer  1 , Panneerselvam Muthuvel  2 , T Mohan Das  1   2
Affiliations

Insights into a novel class of azobenzenes incorporating 4,6- O-protected sugars as photo-responsive organogelators

P V Bhavya et al. RSC Adv. .

Abstract

A novel class of 4,6-O-butylidene/ethylidene/benzylidene β-d-glucopyranose gelator functionalized with photo-responsive azobenzene moieties were designed and synthesized and also characterized using different spectral techniques. These azobenzene-based organogelators can gel even at lower concentrations (critical gelation concentration - 0.5% and 1%). A morphological study of the gels shows one-dimensional aggregated bundles and helical fibres. The main driving force for the self-assembly is through cooperative interactions exhibited by the different groups viz., sugar hydroxyl (hydrogen bonding interaction), azobenzene (aromatic π-π interaction) and alkyl chain of the protecting group (van der Waals interaction).

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Representative examples of sugar-based low molecular weight organogelators reported in the literature.
Scheme 1
Scheme 1. Synthesis of sugar-azo derivatives 5–7, 9–11 & 13–15. Reagents and reaction conditions: (i) toluene, AcOH, 60 °C, 21 h, 70% (ii) 4,6-O-protected d-glucose, 81–88% 1(a–c), ethanol, rt, (iii) KOH, 90 °C, 1 h, 94% (iv) 4,6-O-protected d-glucose 1(a–c), ethanol, rt, 71–83% (v) compound 3, toluene, AcOH, 60 °C, 16% (vi) 4,6-O-protected d-glucose 1(a–c), ethanol, rt, 66–85%.
Fig. 2
Fig. 2. Picture of sol–gel transition of compound 13 in p-xylene (0.5 mg mL−1).
Fig. 3
Fig. 3. SEM and HR-TEM images of compound, 13 from p-xylene: (a) (0.5% w/v p-xylene) solution; (b–d) gel.
Fig. 4
Fig. 4. DSC spectra of compound 13 and its gel in p-xylene.
Fig. 5
Fig. 5. Powder XRD diffraction of xerogel, 13 (p-xylene 0.5%).
Fig. 6
Fig. 6. Absorption spectra of compounds 12 (a), 13 (b) and 15 (c) in acetonitrile (1 × 10−5 M).
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