Araştırma Makalesi
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Yıl 2017, Cilt: 4 Sayı: 2, 501 - 516, 27.03.2017
https://doi.org/10.18596/jotcsa.296370

Öz

Kaynakça

  • 1. Tsujioka T, Irie M. Electrical functions of photochromic molecules. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2010 Mar;11(1):1–14.
  • 2. Rau H, Durr H. Photochromism: molecules and systems. Photochromism, Molecules and Systems. 1990;165–192.
  • 3. Irie M. Diarylethenes for Memories and Switches. Chemical Reviews. 2000 May;100(5):1685–716.
  • 4. Köse M, Orhan E. Comparison of photochromic properties and thermal stabilities of fulgide, fulgimide, and benzimidazole[1,2-a]pyrrolidine-2-one derivatives. Turk J Chem. 2009;33:579–88.
  • 5. Kose M, Orhan E, Büyükgüngör O. Synthesis of novel photochromic methyl cyanoacetate-condensed fulgide derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2007 May;188(2–3):358–63.
  • 6. Kose M, Orhan E. Studies on photochromic benzimidazol[1,2a]pyrrolidin-2-ones from the condensation of 2-methyl-3-benzothienylethylidene-(isopropylidene)succinic anhydride with 1,2-diaminobenzenes. Journal of Photochemistry and Photobiology A: Chemistry. 2006 Jan;177(2–3):170–6.
  • 7. Matsuda K, Irie M. Diarylethene as a photoswitching unit. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2004 Oct;5(2):169–82.
  • 8. Krayushkin M, Ivanov S, Martynkin AY, Lichitsky B, Dudinov A, Uzhinov B. Photochromic dihetarylethenes. 7. Synthesis of bis (thienylazoles), photochromic analogs of diarylethenes. Russian Chemical Bulletin. 2001;50(1):116–121.
  • 9. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T. Photochromism of Thiazole-Containing Triangle Terarylenes. European Journal of Organic Chemistry. 2007 Jul;2007(19):3212–8.
  • 10. Orhan E, 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 Jan;314:164–70.
  • 11. Meng X, Zhu W, Zhang Q, Feng Y, Tan W, Tian H. Novel Bisthienylethenes Containing Naphthalimide as the Center Ethene Bridge: Photochromism and Solvatochromism for Combined NOR and INHIBIT Logic Gates. The Journal of Physical Chemistry B. 2008 Dec 11;112(49):15636–45.
  • 12. Tian H, Wang S. Photochromic bisthienylethene as multi-function switches. Chem Commun. 2007;(8):781–92.
  • 13. Kanazawa R, Nakashima T, Kawai T. Photophysical Properties of a Terarylene Photoswitch with a Donor–Acceptor Conjugated Bridging Unit. The Journal of Physical Chemistry A. 2017 Mar 2;121(8):1638–46.
  • 14. Cheng H-B, Tan X, Pang M-L. Near-Infrared Photochromic Diarylethenes Based on the Changes in the π-Conjugated System and the Electronic Properties of the Heteroaryl Moieties: Near-IR Photochromic Diarylethenes. European Journal of Organic Chemistry. 2013 Dec;2013(35):7933–40.
  • 15. Nakashima T, Goto M, Kawai S, Kawai T. Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium. Journal of the American Chemical Society. 2008 Nov 5;130(44):14570–5.
  • 16. Liu H-H, Chen Y. Modulation of absorption and fluorescence of photochromic diarylethene by intramolecular hydrogen bond. Journal of Physical Organic Chemistry. 2012 Feb;25(2):142–6.
  • 17. Lin Q, Xiao S, Li R, Tan R, Wang S, Zhang R. Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state. Dyes and Pigments. 2015 Mar;114:33–9.
  • 18. Fukaminato T. Single-molecule fluorescence photoswitching: Design and synthesis of photoswitchable fluorescent molecules. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2011 Nov;12(3):177–208.
  • 19. Jiang G, Wang S, Yuan W, Zhao Z, Duan A, Xu C, et al. Photo- and Proton-Dual-Responsive Fluorescence Switch Based on a Bisthienylethene-Bridged Naphthalimide Dimer and Its Application in Security Data Storage. European Journal of Organic Chemistry. 2007 May;2007(13):2064–7.
  • 20. Kose M, Orhan E, Suzuki K, Tutar A, Ünlü CS, Yokoyama Y. Preparation and photochromic properties of 2,3-bisarylbenz[f]indenones. Journal of Photochemistry and Photobiology A: Chemistry. 2013 Apr;257:50–3.
  • 21. Berberich M, Natali M, Spenst P, Chiorboli C, Scandola F, Würthner F. Nondestructive Photoluminescence Read-Out by Intramolecular Electron Transfer in a Perylene Bisimide-Diarylethene Dyad. Chemistry - A European Journal. 2012 Oct 22;18(43):13651–64.
  • 22. Pu S, Li H, Liu G, Liu W, Cui S, Fan C. Synthesis and the effects of substitution upon photochromic diarylethenes bearing an isoxazole moiety. Tetrahedron. 2011 Feb;67(7):1438–47.
  • 23. Kawai S, Nakashima T, Kutsunugi Y, Nakagawa H, Nakano H, Kawai T. Photochromic amorphous molecular materials based on dibenzothienylthiazole structure. Journal of Materials Chemistry. 2009;19(22):3606-3611.
  • 24. Shirinian VZ, Lonshakov DV, Kachala VV, Zavarzin IV, Shimkin AA, Lvov AG, et al. Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones. The Journal of Organic Chemistry. 2012 Sep 21;77(18):8112–23.
  • 25. Morinaka K, Ubukata T, Yokoyama Y. Structurally Versatile Novel Photochromic Bisarylindenone and Its Acetal: Achievement of Large Cyclization Quantum Yield. Organic Letters. 2009 Sep 3;11(17):3890–3.
  • 26. Kose M, Şekerci ÇY, Suzuki K, Yokoyama Y. Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2011 Mar;219(1):58–61.
  • 27. Heller HG, Langan JR. Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene)(isopropylidene)succinic anhydride as a simple convenient chemical actinometer. J Chem Soc, Perkin Trans 2. 1981;(2):341–3.
  • 28. Miyaura N, Yamada K, Suzuki A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Letters. 1979 Jan;20(36):3437–40.

Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors

Yıl 2017, Cilt: 4 Sayı: 2, 501 - 516, 27.03.2017
https://doi.org/10.18596/jotcsa.296370

Öz

The objective of the research was to synthesise new
photo switchable photochromic fluorescence compounds. Starting from
N-butyl-4-bromo-3-iodo-1,8-naphthalimide
new
compounds:

3,4-Bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-Bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-naphthalimide
2O were prepared via two step Suzuki
coupling reaction of aryl boronic acid and esters, and their photochromic
fluorescence properties were investigated. Although all prepared bisaryl
naphthlimides were fluorescence due to the naphthlimide moiety,
among them photochrome 1O
displayed photochromism. On exposure to ultraviolet light, the photochrome 1O showed a pale yellow to blue-green
colour change due to the formation of ring closed form 1C, which reversed to the ring opened form 1O on exposure to visible light. Conversion ratio and quantum
efficiency (from O to C form) for 1O
were also determined.



Additionally,
a solvent effect on the fluorescence properties of 1O and 2O was
investigated. Increase of solvent polarity results in a red shift (to longer
wavelengths) of the fluorescence emissions.

Kaynakça

  • 1. Tsujioka T, Irie M. Electrical functions of photochromic molecules. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2010 Mar;11(1):1–14.
  • 2. Rau H, Durr H. Photochromism: molecules and systems. Photochromism, Molecules and Systems. 1990;165–192.
  • 3. Irie M. Diarylethenes for Memories and Switches. Chemical Reviews. 2000 May;100(5):1685–716.
  • 4. Köse M, Orhan E. Comparison of photochromic properties and thermal stabilities of fulgide, fulgimide, and benzimidazole[1,2-a]pyrrolidine-2-one derivatives. Turk J Chem. 2009;33:579–88.
  • 5. Kose M, Orhan E, Büyükgüngör O. Synthesis of novel photochromic methyl cyanoacetate-condensed fulgide derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2007 May;188(2–3):358–63.
  • 6. Kose M, Orhan E. Studies on photochromic benzimidazol[1,2a]pyrrolidin-2-ones from the condensation of 2-methyl-3-benzothienylethylidene-(isopropylidene)succinic anhydride with 1,2-diaminobenzenes. Journal of Photochemistry and Photobiology A: Chemistry. 2006 Jan;177(2–3):170–6.
  • 7. Matsuda K, Irie M. Diarylethene as a photoswitching unit. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2004 Oct;5(2):169–82.
  • 8. Krayushkin M, Ivanov S, Martynkin AY, Lichitsky B, Dudinov A, Uzhinov B. Photochromic dihetarylethenes. 7. Synthesis of bis (thienylazoles), photochromic analogs of diarylethenes. Russian Chemical Bulletin. 2001;50(1):116–121.
  • 9. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T. Photochromism of Thiazole-Containing Triangle Terarylenes. European Journal of Organic Chemistry. 2007 Jul;2007(19):3212–8.
  • 10. Orhan E, 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 Jan;314:164–70.
  • 11. Meng X, Zhu W, Zhang Q, Feng Y, Tan W, Tian H. Novel Bisthienylethenes Containing Naphthalimide as the Center Ethene Bridge: Photochromism and Solvatochromism for Combined NOR and INHIBIT Logic Gates. The Journal of Physical Chemistry B. 2008 Dec 11;112(49):15636–45.
  • 12. Tian H, Wang S. Photochromic bisthienylethene as multi-function switches. Chem Commun. 2007;(8):781–92.
  • 13. Kanazawa R, Nakashima T, Kawai T. Photophysical Properties of a Terarylene Photoswitch with a Donor–Acceptor Conjugated Bridging Unit. The Journal of Physical Chemistry A. 2017 Mar 2;121(8):1638–46.
  • 14. Cheng H-B, Tan X, Pang M-L. Near-Infrared Photochromic Diarylethenes Based on the Changes in the π-Conjugated System and the Electronic Properties of the Heteroaryl Moieties: Near-IR Photochromic Diarylethenes. European Journal of Organic Chemistry. 2013 Dec;2013(35):7933–40.
  • 15. Nakashima T, Goto M, Kawai S, Kawai T. Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium. Journal of the American Chemical Society. 2008 Nov 5;130(44):14570–5.
  • 16. Liu H-H, Chen Y. Modulation of absorption and fluorescence of photochromic diarylethene by intramolecular hydrogen bond. Journal of Physical Organic Chemistry. 2012 Feb;25(2):142–6.
  • 17. Lin Q, Xiao S, Li R, Tan R, Wang S, Zhang R. Intermolecular hydrogen bonding-assisted high contrast fluorescent switch in the solid state. Dyes and Pigments. 2015 Mar;114:33–9.
  • 18. Fukaminato T. Single-molecule fluorescence photoswitching: Design and synthesis of photoswitchable fluorescent molecules. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2011 Nov;12(3):177–208.
  • 19. Jiang G, Wang S, Yuan W, Zhao Z, Duan A, Xu C, et al. Photo- and Proton-Dual-Responsive Fluorescence Switch Based on a Bisthienylethene-Bridged Naphthalimide Dimer and Its Application in Security Data Storage. European Journal of Organic Chemistry. 2007 May;2007(13):2064–7.
  • 20. Kose M, Orhan E, Suzuki K, Tutar A, Ünlü CS, Yokoyama Y. Preparation and photochromic properties of 2,3-bisarylbenz[f]indenones. Journal of Photochemistry and Photobiology A: Chemistry. 2013 Apr;257:50–3.
  • 21. Berberich M, Natali M, Spenst P, Chiorboli C, Scandola F, Würthner F. Nondestructive Photoluminescence Read-Out by Intramolecular Electron Transfer in a Perylene Bisimide-Diarylethene Dyad. Chemistry - A European Journal. 2012 Oct 22;18(43):13651–64.
  • 22. Pu S, Li H, Liu G, Liu W, Cui S, Fan C. Synthesis and the effects of substitution upon photochromic diarylethenes bearing an isoxazole moiety. Tetrahedron. 2011 Feb;67(7):1438–47.
  • 23. Kawai S, Nakashima T, Kutsunugi Y, Nakagawa H, Nakano H, Kawai T. Photochromic amorphous molecular materials based on dibenzothienylthiazole structure. Journal of Materials Chemistry. 2009;19(22):3606-3611.
  • 24. Shirinian VZ, Lonshakov DV, Kachala VV, Zavarzin IV, Shimkin AA, Lvov AG, et al. Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones. The Journal of Organic Chemistry. 2012 Sep 21;77(18):8112–23.
  • 25. Morinaka K, Ubukata T, Yokoyama Y. Structurally Versatile Novel Photochromic Bisarylindenone and Its Acetal: Achievement of Large Cyclization Quantum Yield. Organic Letters. 2009 Sep 3;11(17):3890–3.
  • 26. Kose M, Şekerci ÇY, Suzuki K, Yokoyama Y. Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2011 Mar;219(1):58–61.
  • 27. Heller HG, Langan JR. Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene)(isopropylidene)succinic anhydride as a simple convenient chemical actinometer. J Chem Soc, Perkin Trans 2. 1981;(2):341–3.
  • 28. Miyaura N, Yamada K, Suzuki A. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Letters. 1979 Jan;20(36):3437–40.
Toplam 28 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik, Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Ersin Orhan

Yayımlanma Tarihi 27 Mart 2017
Gönderilme Tarihi 5 Mart 2017
Kabul Tarihi 27 Mart 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 4 Sayı: 2

Kaynak Göster

Vancouver Orhan E. Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors. JOTCSA. 2017;4(2):501-16.