Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

Abstract

Oxidative coupling polymerization of naphthalene, anthracene, and pyrene with FeCl 3 in nitrobenzene under nitrogen gave polynaphthalene (PNP), polyanthracene (PAT), and polypyrene (PPR) in good yields, respectively. PNP, PAT, and PPR were transformed into sulfonated PNP (S-PNP), S-PAT, and S-PPR by the treatment with chlorosulfonic acid in dichloromethane at 25 C for 24 h under nitrogen, respectively. The activities of S-PPR were higher than those of S-PNP and S-PAT. For the hydrolysis of cyclohexyl acetate and oleyl acetate in water, activities of S-PPR, S-PAT, and S-PNP were considerably higher than those of the other conventional solid acids. Rate constants of S-PPR were 2.8 and 11.7 times larger than those of the sulfonated condensed polynuclear aromatic (S-COPNA(PR)) resin (PR ¼ pyrene) for the hydrolysis of cyclohexyl acetate and oleyl acetate, respectively. S-PPR, S-PAT, and S-PNP were reused without significant loss of activities.

Sulfonated polyanthracene-catalyzed highly efficient and chemoselective thioacetalization of carbonyl compounds and transthioacetalization of acetals and acylals

“…The catalyst shows the high activity in water media for the hydrolysis of esters. [27] There is no example on the use of S-PAT as catalyst for the synthesis of dithioacetals. In continuation of our previous works on the applications of catalysts in the synthesis of organic compounds and thioacetalization of carbonyl groups, [28][29][30][31][32][33][34] we report here S-PAT as a novel and recyclable catalyst for the efficient and chemoselectivity protection of aldehydes as dithioacetals under solvent-free conditions.…”

“…Preparation of acylals, [36][37][38] acetals [39][40][41] and S-PAT [27] was carried out according to previously reported methods. Yields refer to isolated pure products.…”

Sulfonated Pyrene as a Photoregulator for Single‐Stranded DNA Looping

“…PyBA and HSO 3 Cl were used for sulfonation according to the method reported by Lu and Tanemura et al . With ice–water cooling and stirring under Ar atmosphere, a solution of HSO 3 Cl (0.06 mL, 0.9 mmol) in super‐dehydrated dichloromethane (7.5 mL) was added dropwise to a solution of PyBA in dichloromethane (0.13 g, 0.45 mmol), and the mixture was stirred for 2 h. Precipitation was observed during the reaction.…”

Fabrication of a Novel and High-Performance Mesoporous Ethylene Tar-Based Solid Acid Catalyst for the Dehydration of Fructose into 5-Hydroxymethylfurfural

“…31−33 In addition, they have also carried out the experiments in the synthesis of the strongly acidic sulfonated polynaphthalene, polypyrene, and polyanthracene via an oxidative coupling reaction using FeCl 3 in nitrobenzene under nitrogen. 34 These sulfonated condensed polynuclear aromatic (S-COPNA) resins are insoluble in boiling water and many hot organic solvents and can be recycled without an obvious loss of activity. Moreover, the activity of S-COPNA resins is much higher than that of conventional solid acids.…”