Synthesis of 1,2-bis[2-methyl-5(3,4-difluorophenyl)-3-thienyl]perfluorocyclopentene

Abstract

2-Methylthiophene (1) was treated at 0°C with liquid bromine to form 3,5-dibromo-2-methylthiophene (2) which reacted with tributyl borate to give 2-methyl-3-bromo-5-boronate thiophene (3) at -78°C. Treatment of 3 with 3,4-difluorobrombenzene gave 2-methyl-3-bromo-5-(3,4-difluorophenyl)thiophene (4). Finally, a novel photochromic dithienylethene compound, 1,2-bis[2-methyl-5(3,4-difluorophenyl)-3-thienyl]perfluorocyclopentene (DT-1), was synthesized by the reaction of 4 with perfluorocyclopentene at -78°C. The compound (DT-1) was characterized by IR, NMR, MS, elemental analysis and its photochromic behavior was also discussed.

References

1. Irie M Mohri M Thermally irreversible photochromicsystems. Reversible photocyclization of diarylethene derivatives.J Org Chem 1988 53803808. doi:10.1021/jo00239a022
2. Nakayama Y Hayashi K Irie M Thermally irreversible photochromic systems. Reversiblephotocyclization of 1,2-diselenenylethene and 1,2-diindolylethenederivativesJ Org Chem 1990 5525922596. doi:10.1021/jo00296a011
3. Irie M Moleculardesign and synthesis of photochromic diarylethenesYuki Gosei Kagaku Kyokaishi 1991 49(5)373382
4. Nakayama Y Hayashi K Irie M Thermally Irreversible Photochromic Systems. ReversiblePhotocyclization of non-symmetric diarylethene derivativesBull Chem Soc Jpn 1991 64789795. doi:10.1246/bcsj.64.789
5. Nakayama Y Hayashi K Irie M Thermally irreversible photochromic systems. Photoreactionof diarylethene derivatives with imidazo[1,2-a]pyridine ringsBull Chem Soc Jpn 1991 64202207. doi:10.1246/bcsj.64.202
6. Nakamura S Irie M Thermally irreversible photochromicsystems. A theoretical studyJ Org Chem 1988 5361366138. doi:10.1021/jo00261a035
7. Nakayama Y Irie M Photocontraction of polyethylene-containingphotochromic dyesSenryo to Yohokin 1990 35(11)298306
8. Irie M Advancesin photochromic materials for optical data storage mediaJpn Appl Phys 1989 28215219. doi:10.1143/JJAP.28.1504
9. Irie M Uchida T Tsuzuki H Photochromism of single crystalline diarylethenesChem Lett 1995 899900
10. Irie M Uchida K Synthesis and properties ofphotochromic diarylethenes with heterocyclic aryl groupsBull Chem Soc Jpn 1998 71985996. doi:10.1246/bcsj.71.985
11. Naoto T Hiroshi M Ultrafast dynamics of photochromicsystemsChem Rev 2000 10018751890. doi:10.1021/cr9800816
12. Irie S Irie M Radiation-Induced colorationof photochromic dithienylethene derivatives in polymer matricesBull Chem Soc Jpn 2000 7323852388. doi:10.1246/bcsj.73.2385
13. Irie M Diarylethenesfor memories and switchesChem Rev 2000 10016851716. doi:10.1021/cr980069d
14. Ern J Bens A T Martin H D Reaction dynamics of photochromic dithienylethene derivativesChem Phys 1999 246115125. doi:10.1016/S0301‐0104(99)00183‐4