Fragility and Tendency to Crystallization for Structurally Related Compounds
Abstract
:1. Introduction
2. Results and Discussion
2.1. Calorimetric Study of Tendency to Crystallize
- Class I. For (S)-NOO, crystallization was observed during cooling from the melt (see Figure 1a). It is a poor glass former that requires exceeding a critical cooling rate (~30 K/min) for the successful formation of glass.
- Class II. (S)-NSS did not crystallize during cooling from the melt to below Tg, but easily crystallized during subsequent reheating above Tg (see Figure 1b).
- Class III. For (S)-NOS, no crystallization was observed, either during the quenching from the melt or during the reheating cycle (see Figure 1c). This compound is characterized by the best physical stability among those tested.
2.2. Molecular Dynamics Investigations (Dielectric Study)
2.3. Thermodynamic Fragility (Calorimetric Study)
2.4. Isothermal Crystallization Kinetics (Dielectric Study)
3. Materials and Methods
3.1. Materials
3.2. Standard Differential Scanning Calorimetry
3.3. Stochastic Temperature-Modulated Differential Scanning Calorimetry (TOPEM®)
3.4. Broadband Dielectric Spectroscopy
4. Conclusions
- (i)
- For (S)-4-Benzyl-2-oxazolidinone [(S)-NOO)], the crystallization process is observed during cooling from the melt;
- (ii)
- (S)-4-Benzylthiazolidine-2-thione [(S)-NSS] does not crystallize during cooling from the melt to below Tg, but easily crystallizes during subsequent reheating above Tg;
- (iii)
- For (S)-4-Benzyloxazolidine-2-thione ((S)-NOO), no crystallization is observed, either during the quenching from the melt or during the reheating cycle.
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Material | Physical Stability | VFT Parameters | Tg [K] BDS (for τα = 100 s) | ||
---|---|---|---|---|---|
log(τ0/s) | A [K] | T0 [K] | |||
(S)-NOS | Class III | −14.77 ± 0.24 | 1860 ± 80 | 218 ± 2 | 265.9 ± 0.2 |
(S)-NSS | Class II | −14.80 ± 0.02 | 1830 ± 30 | 216 ± 1 | 262.8 ± 0.1 |
(S)-NOO | Class I | −14.70 ± 0.01 | 1720 ± 20 | 204 ± 1 | 248.9 ± 0.1 |
Material | Molecular Weight [g/mol] & Chemical Structure | Physical Stability | Ea at Tg [kJ/mol] (for τα = 100 s) | Strength Parameter D | Dynamic Fragility m (for τα = 100 s) | Thermodynamic Fragility Moynihan Model |
---|---|---|---|---|---|---|
(S)-NOS | Mw = 193.27 | Class III | 471 ± 8 | 8.55 ± 0.43 | 93 ± 2 | 69 ± 2 |
(S)-NSS | Mw = 209.33 | Class II | 470.0 ± 0.7 | 8.48 ± 0.25 | 93 ± 1 | 125 ± 4 |
(S)-NOO | Mw = 177.20 | Class I | 443.4 ± 0.3 | 8.40 ± 0.13 | 93 ± 1 | 125 ± 4 |
Material | Tm [K] Standard DSC | ΔHm [J/g] Standard DSC | Tg [K] TOPEM® | ΔCp [J/gK] TOPEM® | [K] | [K] | ΔH* at Tg (a) [kJ/mol] |
---|---|---|---|---|---|---|---|
(S)-NOS CLASS III | 338.7 ± 0.5 | 61 ± 1 | 268.0 ± 0.1 | 0.61 ± 0.03 | 261.8 ± 0.1 | 270.1 ± 0.1 | 354.6 |
(S)-NSS CLASS II | 363.8 ± 0.5 | 91 ± 2 | 263.9 ± 0.1 | 0.57 ± 0.03 | 263.4 ± 0.1 | 268.0 ± 0.1 | 635.1 |
(S)-NOO CLASS I | 361.1 ± 0.5 | 115 ± 3 | 251.0 ± 0.1 | 0.58 ± 0.03 | 248.9 ± 0.1 | 253.2 ± 0.1 | 602.4 |
(S)-NOO | |||
Crystallization Temperature [K] | n | t0 [s] | k [s−1] |
291.15 | 3.84 ± 0.11 | 2458 ± 99 | 2.54·10−4 ± 6.6 × 10−6 |
287.15 | 3.30 ± 0.13 | 3533 ± 15 | 2.11·10−4 ± 1.5 × 10−6 |
281.15 | 3.37 ± 0.06 | 5100 ± 220 | 7.26·10−5 ± 1.2 × 10−6 |
277.15 | 3.38 ± 0.07 | 8900 ± 330 | 5.22·10−5 ± 9.2 × 10−7 |
275.15 | 3.40 ± 0.15 | 30,900 ± 100 | 2.29·10−5 ± 5.6 × 10−8 |
(S)-NSS | |||
299.15 | 1.41 ± 0.01 | 124 ± 25 | 1.64·10−4 ± 9 × 10−7 |
295.15 | 1.36 ± 0.01 | 727 ± 40 | 9.38·10−5 ± 5 × 10−7 |
291.15 | 1.38 ± 0.01 | 3284 ± 24 | 5.36·10−5 ± 9 × 10−8 |
287.15 | 1.90 ± 0.05 | 8959 ± 67 | 3.36·10−5 ± 9 × 10−8 |
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Grzybowska, K.; Wojnarowska, Z.; Grzybowski, A.; Paluch, M. Fragility and Tendency to Crystallization for Structurally Related Compounds. Int. J. Mol. Sci. 2024, 25, 3200. https://doi.org/10.3390/ijms25063200
Grzybowska K, Wojnarowska Z, Grzybowski A, Paluch M. Fragility and Tendency to Crystallization for Structurally Related Compounds. International Journal of Molecular Sciences. 2024; 25(6):3200. https://doi.org/10.3390/ijms25063200
Chicago/Turabian StyleGrzybowska, Katarzyna, Zaneta Wojnarowska, Andrzej Grzybowski, and Marian Paluch. 2024. "Fragility and Tendency to Crystallization for Structurally Related Compounds" International Journal of Molecular Sciences 25, no. 6: 3200. https://doi.org/10.3390/ijms25063200