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Scheme 8. Reaction of pyrogallol and 1,5-pentanedial.

Figure 16 Reaction of pyrogallol and 1,5-pentanedial.

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Application of a dynamic covalent chemistry strategy to the reversible reaction system of resorcinol and a, w-alkanedials E-mail: kudoh @kansai-u.ac.jp
Application of a dynamic covalent chemistry strategy to the reversible reaction system of resorcinol and a, w-alkanedials E-mail: kudoh @kansai-u.ac.jp
This highlight review focuses on DCC systems comprising the addition condensation reaction of phenols and dialdehydes. Scheme 1. Reaction of resorcinol and aldehydes.
This highlight review focuses on DCC systems comprising the addition condensation reaction of phenols and dialdehydes. Scheme 1. Reaction of resorcinol and aldehydes.
Scheme 2. Reaction of resorcinol and 1,5-pentanedial. Only cross-linked products could be obtained at reaction temperatures below 40°C, but the amount of cross-linked products decreased as the reaction temperature was increased, and only a soluble product was obtained in 20% yield at 80°C. "HNMR, '3CNMR, IR, and MALDI-TOF mass spectroscopic
Scheme 2. Reaction of resorcinol and 1,5-pentanedial. Only cross-linked products could be obtained at reaction temperatures below 40°C, but the amount of cross-linked products decreased as the reaction temperature was increased, and only a soluble product was obtained in 20% yield at 80°C. "HNMR, '3CNMR, IR, and MALDI-TOF mass spectroscopic
Figure 2. Top and side view of Noria. Figure 1. Effect of reaction temperature on the addition con- densation reaction of resorcinol and 1,5-pentanedial at the feed of resorcinol/1,5-pentanedial = 2/1 for 48h. m; Cross-linked materials, @; soluble low-molecular-weight compound (Noria).
Figure 2. Top and side view of Noria. Figure 1. Effect of reaction temperature on the addition con- densation reaction of resorcinol and 1,5-pentanedial at the feed of resorcinol/1,5-pentanedial = 2/1 for 48h. m; Cross-linked materials, @; soluble low-molecular-weight compound (Noria).
Figure 4. 'HNMR spectrum of poly(Re-co-Pe) (M, = 4,200, M,,/M, = 1.46). Scheme 3. Synthesis of poly(Re-co-Pe) by the addition condensation reaction of resorcinol and 1,5-pentanedial in the feed ratio of resorcinol/1,5-pentanedial = 1/2.
Figure 4. 'HNMR spectrum of poly(Re-co-Pe) (M, = 4,200, M,,/M, = 1.46). Scheme 3. Synthesis of poly(Re-co-Pe) by the addition condensation reaction of resorcinol and 1,5-pentanedial in the feed ratio of resorcinol/1,5-pentanedial = 1/2.
Figure 3. Yields of Noria at 1,5-pentanedial/resorcinol feed ratios of 1/20-10/20 at 80°C for 48h.
Figure 3. Yields of Noria at 1,5-pentanedial/resorcinol feed ratios of 1/20-10/20 at 80°C for 48h.
Figure 5. TGA curves of poly(Re-co-PE) (M, = 4,200, M,,/M, = 1.46) and Noria.
Figure 5. TGA curves of poly(Re-co-PE) (M, = 4,200, M,,/M, = 1.46) and Noria.
Figure 6. SEC profiles of the products obtained by the reaction of poly(Re-co-Te) and resorcinol in the presence of HCI solution in ethanol at 80°C.
Figure 6. SEC profiles of the products obtained by the reaction of poly(Re-co-Te) and resorcinol in the presence of HCI solution in ethanol at 80°C.
Scheme 4. Mechanism of formation of Noria from resorcinol and 1,5-pentanedial.
Scheme 4. Mechanism of formation of Noria from resorcinol and 1,5-pentanedial.
Table 2. Yields and melting points of cyclic oligomer derivatives (Noria-EE, calixarene-dimer[n]-EE, and calixarene- trimer[n]-EE) *M.P = melting point temperature.
Table 2. Yields and melting points of cyclic oligomer derivatives (Noria-EE, calixarene-dimer[n]-EE, and calixarene- trimer[n]-EE) *M.P = melting point temperature.
Table 1. Addition condensation reaction of resorcinol and o,@- alkanedial* “The reaction of resorcinol (20mmol) with a, w-alkanedial (5 mmol) was carried out in the presence of conc.HCl solution (1.5 mL) in ethanol (4.5 mL) for 48h. *4, = 5,700, My /M, = 2.91, estimated by SEC (DMF) based on polystyrene standards. Noria was obtained in 83% yield. “Methanol-insoluble part.
Table 1. Addition condensation reaction of resorcinol and o,@- alkanedial* “The reaction of resorcinol (20mmol) with a, w-alkanedial (5 mmol) was carried out in the presence of conc.HCl solution (1.5 mL) in ethanol (4.5 mL) for 48h. *4, = 5,700, My /M, = 2.91, estimated by SEC (DMF) based on polystyrene standards. Noria was obtained in 83% yield. “Methanol-insoluble part.
Scheme 5. Reaction of resorcinol and 1,4-butanedial.
Scheme 5. Reaction of resorcinol and 1,4-butanedial.
Scheme 6. Reaction of resorcinol and a, w-alkanedial [OHC- (CH»)-CHO, m = 4, 6, 8, and 10].
Scheme 6. Reaction of resorcinol and a, w-alkanedial [OHC- (CH»)-CHO, m = 4, 6, 8, and 10].
Scheme 7. Reaction of resorcinol and a, w-alkanedial [OHC- (CH»)m-CHO, m = 5, 7, and 9].
Scheme 7. Reaction of resorcinol and a, w-alkanedial [OHC- (CH»)m-CHO, m = 5, 7, and 9].
Figure 7. Relationship between melting point temperature and number of methylene chains of a, w-alkanedials.
Figure 7. Relationship between melting point temperature and number of methylene chains of a, w-alkanedials.
Scheme 9. Reaction of 3-alkoxyphenol and 1,5-pentanedial. Scheme 10. Reaction of 2-methylresorcinol and m-benzene- carbaldehyde.
Scheme 9. Reaction of 3-alkoxyphenol and 1,5-pentanedial. Scheme 10. Reaction of 2-methylresorcinol and m-benzene- carbaldehyde.
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