Mahmut KÖSE, Leyla ÖZTÜRK, Khamis Nassor ALLY

Photochromic and fluorescence properties of coumarin fulgimides

Four new fulgimides possessing a fluorescent coumarin unit were synthesized from the corresponding fulgides, and their photochromic as well as fluorescence properties were investigated. The open-ring forms of coumarin fulgimides were found to exhibit fluorescence in the visible region. Upon exposure to UV light, the fulgimides were transformed into the nonfluorescent closed-ring forms, which can be reverted to the initial fluorescent open-ring forms on exposure to visible light. The efficiency of quenching of fluorescence was as high as 95% at the photostationary state of UV irradiation.

PDF

___

1. Dürr H, Bouas-Laurent H. Photochromism: Molecules and Systems. New York, NY, USA: Elsevier, 1990.
2. Yokoyama Y. Fulgides for memories and switches. Chemical Reviews 2000; 100 (5): 1717-1739. doi: 10.1021/cr980070c
3. Yokoyama Y, Kose M. Fulgides and Related Systems. In: Horspool W, Francesco LF (editors). CRC Handbook of Organic Photochemistry and Photobiology. Boca Raton, FL, USA: CRC Press, 2003, pp.1-13.
4. Irie M. Diarylethenes for memories and switches. Chemical Reviews 2000; 100 (5): 1685-1716. doi: 10.1021/cr980069d
5. Irie M, Fukaminato T, Matsuda K, Kobatake S. Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chemical Reviews 2014; 114 (24): 12174-12277. doi: 10.1021/cr500249p
6. Lvov AG, Yokoyama Y, Shirinian VZ. Post-modification of the ethene bridge in the rational design of photochromic diarylethenes. The Chemical Record 2019; 19: 1-14. doi: 10.1002/tcr.201900015
7. Heller HG, Koh K, Elliot C, Whittall J. Fulgides and fulgimides for practical applications. Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 1994; 246: 79-86. doi: 10.1080/10587259408037792
8. Liang Y, Dvornikov AS, Rentzepis PM. Synthesis and properties of photochromic fluorescing 2-indolyl fulgide and fulgimide copolymers. Macromolecules 2002; 35 (25): 9377-9382. doi: 10.1021/ma020750o
9. Köse M, Orhan E. Comparison of photochromic properties and thermal stabilities of fulgide, fulgimide, and benzimidazole[1,2-a]pyrrolidine-2-one derivatives. Turkish Journal of Chemistry 2009; 33: 579-588. doi: 10.3906/kim0805-1.
10. Raymo FM, Tomasulo M. Fluorescence modulation with photochromic switches. The Journal of Physical Chemistry A 2005; 109 (33): 7343-7352. doi: 10.1021/jp052440o
11. Fukaminato T, Ishida S, Métivier RI. Photochromic fluorophores at the molecular and nanoparticle levels: fundamentals and applications of diarylethenes. NPG Asia Materials 2018; 10: 859-881. doi: 10.1038/s41427-018-0075-9
12. Lachmann D, Lahmy R, König B. Fulgimides as light-activated tools in biological investigations. European Journal of Organic Chemistry 2019; 5018-5024. doi: 10.1002/ejoc.201900219
13. Liang Y, Dvornikov AS, Rentzepis PM. Synthesis of novel photochromic fluorescing 2-indolylfulgimides. Tetrahedron Letters 1999; 40: 8067-8069. doi: 10.1016/S0040-4039(99)01702-5
14. Dvornikov AS, Liang Y, Cruse CS, Rentzepis PM. Spectroscopy and kinetics of a molecular memory with nondestructive readout for use in 2D and 3D storage systems. The Journal of Physical Chemistry B 2004; 108 (25): 8652-8658. doi: 10.1021/jp031074a
15. Dvornikov AS, Walker EP, Rentzepis PM. Two-photon three-dimensional optical storage memory. The Journal of Physical Chemistry A 2009; 113 (49): 13633-13644. doi: 10.1021/jp905655z
16. Sivasankaran N, Palaninathan K. Photochromic switchable pendant indolyl fulgimide polypyrrole. Polymer Degradation and Stability 2013; 98 (9): 1852-1861. doi: 10.1016/j.polymdegradstab.2013.05.009
17. Ziarani GM, Moradi R, Lashgari N, Kruger HG. Chapter 7-Coumarin Dyes. In: Metal-Free Synthetic Organic Dyes. 1st edition. Amsterdam, etherlands : Elsevier, 2018, pp.117-125.
18. Walz J, Ulrich K, Port H, Wolf HC, Wonner J et al. Fulgides as switches for intramolecular energy transfer. Chemical Physics Letters 1993; 213 (3-4): 321-324. doi: 10.1016/0009-2614(93)85139-F
19. Darcy PJ, Heller HG, Strydom PJ, Whittall J. Photochromic heterocyclic fulgides. Part 2. Electrocyclic reactions of (E)-α-2,5-dimethyl-3-furylethylidene(alkyl-substituted methylene)succinic anhydrides. Journal of the Chemical Society, Perkin Transactions 1 1981; 202-205. doi: 10.1039/P19810000202
20. Yokoyama Y, Hayata H, Ito H, Kurıta Y. Photochromism of a furylfulgide, 2-[1-(2,5-Dimethyl-3-furyl)ethylidene]- 3-isopropylidenesuccinic anhydride in solvents and polymer films. Bulletin of the Chemical Society of Japan 1990; 63: 1607-1610. doi: 10.1246/bcsj.63.1607
21. Reichardt C. Solvatochromic dyes as solvent polarity indicators. Chemical Reviews 1994; 94 (8): 2319-2358. doi: 10.1021/cr00032a005
22. Tian W, Tian J. An insight into the solvent effect on photo-, solvato- chromism of spiropyran through the perspective of intermolecular interactions. Dyes and Pigments 2014; 105: 66-74. doi: 10.1016/j.dyepig.2014.01.020
23. Ersin O, Gundogdu L, Kose M, Yokoyama Y. Synthesis and photochromic properties of 4,5-bisaryl-3(2H)- pyridazinones. Journal of Photochemistry and Photobiology A: Chemistry 2016; 314: 164-170. doi: 10.1016/j.jphotochem.2015.08.025
24. Liang Y, Dvornikov AS, Rentzepis PM. Synthesis and photochemistry of photochromic fluorescing indol-2- ylfulgimides. Journal of Materials Chemistry 2000; 10 (11): 2477-2482. doi: 10.1039/B002374O
25. Heller HG, Langan RJ. Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene) (isopropylidene)succinic anhydride as a simple convenient chemical actinometer. Journal of the Chemical Society, Perkin Transactions 2 1981; 341-343. doi: 10.1039/P29810000341
26. Cyraňski MK, Krygowski TM, Katritzky AR, Schleyer PvR. To what extent can aromaticity be defined uniquily? The Journal of Organic Chemistry 2002; 67: 1333-1338. doi: 10.1021/jo016255s
27. Rybalkin VP, Zmeeva SY, Popova LL, Tikhomirova KS, Revinskii YV et al. Photochromic benzo[g]indolyl fulgimide with modulated fluorescence. Russian Journal of Organic Chemistry 2017; 53 (1): 29-34. doi: 10.1134/S1070428017010067