Methanol → Anthracene

Clear solutions of 2,6-pyridinedicarbonyl dichloride (84 mg, 0.41 mmol) in 15 mL of chloroform and 9,10-bis(aminomethyl)anthracene (97 mg, 0.41 mmol) in 15 mL of chloroform were simultaneously added dropwise over 10 h to a stirred solution of squaraine 13a (32 mg, 0.05 mmol, synthesized according to E. Arunkumar et al. Chem. Eur. J. 2006, 12, 4884-4690) and triethylamine (81 mg, 0.8 mmol) in 30 mL of chloroform. After overnight stirring, the mixture containing rotaxane 13 and polymer co-products was filtered, washed with chloroform (100 mL) to extract rotaxane 13, and the filtrate was concentrated. Purification of the crude material by column chromatography using silica gel (gradient, 0-1% of MeOH in CHCl3) gave the rotaxane 13. λmax (abs): 651 m, λmax (em): 707 nm, 59% (methanol); λmax (abs): 648 nm, λmax (em): 700 nm, Q.Y.: 65% (chloroform).

1. additionthe mixture containing rotaxane 13 and polymer co-products
2. filtrationwas filtered
3. washwashed with chloroform (100 mL)
4. extractionto extract rotaxane 13
5. concentrationthe filtrate was concentrated
6. customPurification of the crude material by column chromatography
7. customgave the rotaxane 13

ORDレコード

ord-fd0c4243253a42aca4db30ba11b3a6d1

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08642014B2