Potassium carbonate

The monomer4,5-dichlorophthalic anhydride was purchased from Tokyo Chemical Industry (TCI) Co. Ltd. (Tokyo, Japan); 5,5′,6,6′-tetrahydroxy-3,3,3,3′-tetramethyl-1,1′-spirobisindane (97%) was purchased from Alfa Aesar (Seoul, Korea). These were used as obtained. Zirconium chloride (ZrCl₄) and 2-aminoterephthalic acid were obtained from Alfa Aesar (Seoul, Korea). Pebax was purchased from ArkemaInc. Methanol, ethanol, chloroform, dimethyl formamide, and potassium carbonate were purchased from DaeJung Chemicals & Metals Co. Ltd. (Shiheung, Korea) in South Korea. Acetic anhydride, acetic acid, and triethylamine were obtained from Sigma Aldrich. (Yongin, Korea)

Chemicals: Choline chloride, phosphoryl oxychloride, potassium carbonate, and celite were purchased from Daejung Chemicals & Metals Co., Ltd., Siheung, Republic of Korea. (R)-( $-$ )-3-chloro-1,2-propanediol was purchased from TCI. All other chemicals were purchased from Merck.
Flow system: All parts of the system were manually assembled to customize the continuous flow reactor. Chemyx Fusion 200 syringe pumps were used for reactants injection. Among the system components, shut-off valve, static mixing tee, 4-port 3-way flow-switching valves and unions were purchased from Upchurch Scientific. Gastight borosilicate glass syringes (10 mL and 25 mL volumes) and 1/32″ ID tubing (PTFE) were purchased from Runze Fluid. The product-collecting vials located at the end of the system were 50 mL borosilicate vials, purchased from Samwoo Kurex.

10,12-Pentacosadiynoic acid (PCDA) was purchased from GFS Chemicals (Ohio, USA). Lithium aluminum hydride (LiAlH₄), tetrabromomethane, triphenylphosphine, potassium iodide, and 4-dimethylaminopyridine (DMAP) were purchased from Sigma-Aldrich. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC) was purchased from TCI chemicals (Tokyo, Japan). Potassium carbonate, sodium hydroxide, and sodium nitrite were purchased from Daejung Chemicals & Metals (Seoul, South Korea). Hydrochloric acid and methyl-4-aminobenzoate were purchased from Fisher Scientific (Massachusetts, USA). The detailed synthetic protocols for DA-Azo-TEG and spectral data are provided in Supporting Information.