Investigation of [2+2] photodimerization of trans-4-(trifluoromethyl) cinnamic acid

Authors

  • Ulambayar Bayasgalan Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia
  • Bariashir Chantsalnyam Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia https://orcid.org/0000-0002-8912-2156
  • Uranbileg Nergui Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia
  • Batchuluun Khongorzul Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia
  • Lkhasuren Jargalsaikhan Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia
  • Jav Davaasambuu Institute of Physics and Technology, Mongolian Academy of Sciences, Ulaanbaatar, 13330, Mongolia

DOI:

https://doi.org/10.5564/bicct.v10i10.2597

Keywords:

solid-state, dimerization, x-ray diffraction, photochemistry

Abstract

Solid state [2+2] photodimerization is one of the unique organic reactions that take place between unsaturated molecules under ambient conditions. Complex molecules that are difficult to obtain by traditional organic synthesis methods can be obtained in high yield without the use of solvents. In this work, solid-state [2+2] photodimerization of trans-4-trifluoromethyl cinnamic was investigated via X-ray diffraction and optical spectroscopy methods (UV-vis spectroscopy, FTIR spectroscopy). The crystal structure was determined from powder X-ray diffraction. Furthermore, optical spectroscopy results indicate that the trans-4-trifluoromethyl cinnamic acid undergoes [2+2] photodimerization reaction to yield a product with a cyclobutane framework. The photoconversion process is associated with a complete loss of the long-range order of the reactant and the resulting material is amorphous. Due to the utilization of broad-band light for the reaction, large amounts of product form on the surface and this leads to the precipitation of the product phase which disintegrates the crystal.

Транс-4-трифлуорометил фенилпропионы хүчлийн [2+2] фотодимеризаци урвалын судалгаа

Хураангуй: Тасалгааны орчинд гэрлийн үйлчлэлээр давхар холбоо бүхий ханаагүй молекул хооронд явагддаг органик
химийн өвөрмөц урвалуудын нэг нь [2+2]фотодимеризацийн урвал юм. Энэ урвалыг хатуу төлөвт явуулснаар уламжлалт
органик синтезийн аргуудаар гарган авахад хүндрэлтэй комплекс молекулуудыг хортой уусгагч ашиглалгүйгээр, өндөр
гарцтайгаар гарган авах боломжтой. Бид энэ ажлаар транс-4-трифлуорометил фенилпропионы хүчлийн кристаллын
тасалгааны температурт явагдах хатуу төлөвийн [2+2] фотодимеризацийн урвалын судалгааг нунтгийн рентген дифракци ба
оптик спектроскопын аргуудаар (хэт ягаан туяа-үзэгдэх гэрлийн спектроскоп, нил улаан туяаны спектроскоп) хийж
гүйцэтгэсэн. Транс-4-трифлуорометил фенилпропионы хүчлийн кристалл бүтцийг нунтгийн рентген дифракцийн аргаар
тодорхойлсон. Цаашлаад, транс-4-трифлуорометил фенилпропионы хүчил нь [2+2] фотодимеризацийн урвалд орж
циклобутан бүхий молекул үүсгэдэг болохыг оптик спектроскопын үр дүнгээр харуулав. Урвалын явцад дээжийн кристалл
бүтэц алдагдаж шинэ аморф бүтэц үүсэж буйг нунтгийн рентген дифракцийн аргаар батлав. Энэ үзэгдлийг транс-4-
трифлуорометил фенилпропионы хүчлийн кристаллыг өргөн мужийн гэрлээр үйлчилэх үед кристаллын гадаргууд үүссэн их
хэмжээний бүтээгдэхүүн бодис нь тунадасжиж шинэ фаз үүссэнтэй холбон тайлбарлав.

Түлхүүр үг: хатуу төлөв, димеризаци, рентген дифракци, фотохими

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References

Jacquemin, P.-L., Robeyns, K., Devillers, M., & Garcia, Y. (2014). Reversible photochromism of an N-salicylidene aniline anion. Chem. Commun., 50(6), 649–651. https://doi.org/10.1039/c3cc45080e

Wang, C., Li, P., Zhang, S., Zhang, G., Tan, S., W, Y., & Watanabe, M. (2020). Azobenzene Molecule Trigger Controlling Phase Transitions of PNIPAm in Ionic Liquids and Light-Controlled Adhesiveness. Macromolecules, 53(12), 4901-4907. https://doi.org/10.1021/acs.macromol.0c00652

Gan, M.-M., Yu, J.-G., Wang, Y.-Y., & Han, Y.-F. (2018). Template-Directed Photochemical [2 + 2] Cycloaddition in Crystalline Materials: A Useful Tool to Access Cyclobutane Derivatives. Crystal Growth & Design, 18(2), 553-565. https://doi.org/10.1021/acs.cgd.7b01308

Biradha, K., & Santra, R. (2013). Crystal engineering of topochemical solid state reactions. Chem. Soc. Rev., 42(3), 950–967. https://doi.org/10.1039/c2cs35343a

Khoj, M. A., Hughes, C. E., Harris, K. D. M., & Kariuki, B. M. (2013). Polymorphism in a trans-Cinnamic Acid Derivative Exhibiting Two Distinct β-type Phases: Structural Properties, [2 + 2] Photodimerization Reactions, and Polymorphic Phase Transition Behavior. Crystal Growth & Design, 13(9), 4110–4117. https://doi.org/10.1021/cg4009202

Cohen, M. D., Schmidt, G. M. J., & Sonntag, F. I. (1964). 384. Topochemistry. Part II. The photochemistry of trans- cinnamic acids. Journal of the Chemical Society (Resumed), 2000. https://doi.org/10.1039/jr9640002000

Schmidt, G. M. J. (1971). Photodimerization in the solid state. Pure and Applied Chemistry, 27(4), 647–678. https://doi.org/10.1351/pac197127040647

Murthy, G. S., Arjunan, P., Venkatesan, K., & Ramamurthy, V. (1987). Consequences of lattice relaxability in solid state photodimerizations. Tetrahedron, 43(7), 1225–1240. https://doi.org/10.1016/s0040-4020(01)90245-5

d’Agostino, S., Spinelli, F., Boanini, E., Braga, D., & Grepioni, F. (2016). Single crystal to single crystal [2+2] photoreactions in chloride and sulphate salts of 4-amino-cinnamic acid via solid-solution formation: a structural and kinetic study. Chemical Communications, 52(9), 1899–1902. https://doi.org/10.1039/c5cc09412g

d’Agostino, S., Boanini, E., Braga, D., & Grepioni, F. (2018). Size Matters: [2 + 2] Photoreactivity In Macro- and Microcrystalline Salts of 4-Aminocinnamic Acid. Crystal Growth & Design, 18(4), 2510–2517. https://doi.org/10.1021/acs.cgd.8b00109

Ito, Y., Borecka, B., Trotter, J., & Scheffer, J. R. (1995). Control of solid-state photodimerization of trans-cinnamic acid by double salt formation with diamines. Tetrahedron Letters, 36(34), 6083–6086. https://doi.org/10.1016/0040-4039(95)01209-z

Coates, G. W., Dunn, A. R., Henling, L. M., Ziller, J. W., Lobkovsky, E. B., & Grubbs, R. H. (1998). Phenyl−Perfluorophenyl Stacking Interactions: Topochemical [2+2] Photodimerization and Photopolymerization of Olefinic Compounds. Journal of the American Chemical Society, 120(15), 3641–3649. https://doi.org/10.1021/ja974072a

Koivukorpi, J., & Kolehmainen, E. (2009). UV-induced solvent free synthesis of truxillic acid–bile acid conjugates. Journal of Molecular Structure, 930(1-3), 116–120. https://doi.org/10.1016/j.molstruc.2009.05.001

Busse, G., Tschentscher, T., Plech, A., Wulff, M., Frederichs, B., & Techert, S. (2002). First investigations of the kinetics of the topochemical reaction of p-formyl-trans-cinnamic acid by time-resolved X-ray diffraction. Faraday Discussions, 122, 105–117. https://doi.org/10.1039/b202831j

Howard, J. A. K., & Sparkes, H. A. (2008). Trans-4-(trifluoromethyl) cinnamic acid: Structural characterisation and crystallographic investigation into the temperature induced phase transition. CrystEngComm, 10(5), 502. https://doi.org/10.1039/b715349j

Davaasambuu, J., Busse, G., & Techert, S. (2006). Aspects of the Photodimerization Mechanism of 2,4- Dichlorocinnamic Acid Studied by Kinetic Photocrystallography. The Journal of Physical Chemistry A, 110(9), 3261–3265. https://doi.org/10.1021/jp054723m

Giunchi, A., Pandolfi, L., Salzillo, T., Brillante, A., Della Valle, R. G., d’Agostino, S., & Venuti, E. (2022). Visualizing a Single‐Crystal‐to‐Single‐Crystal [2+2] Photodimerization through its Lattice Dynamics: An Experimental and Theoretical Investigation. ChemPhysChem, 23(12). https://doi.org/10.1002/cphc.202200168

Enkelmann, V., Wegner, G., Novak, K., & Wagener, K. B. (1993). Single-crystal-to-single-crystal photodimerization of cinnamic acid. Journal of the American Chemical Society, 115(22), 10390–10391. https://doi.org/10.1021/ja00075a077

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Published

2022-12-24

How to Cite

Bayasgalan, U., Chantsalnyam, B., Nergui, U., Khongorzul, B., Jargalsaikhan, L., & Davaasambuu, J. (2022). Investigation of [2+2] photodimerization of trans-4-(trifluoromethyl) cinnamic acid. Bulletin of the Institute of Chemistry and Chemical Technology, 10(10), 75–79. https://doi.org/10.5564/bicct.v10i10.2597

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