Design and TDDFT study of the novel structures similar to BODIPY with prominent fluorescence properties

Document Type : Research Paper

Authors

1 Department of Chemistry, Tuyserkan Branch, Islamic Azad University, Tuyserkan, Iran

2 Department of Chemistry, Lorestan University, Khorramabad, Iran

10.22034/ijnc.2022.1.4

Abstract

Functional dye is a new term in the field of dye chemistry which has been specifically designed for high-technology applications such as solar cells, photochromic dyes, liquid crystal, electrophotography, fluorescent sensors and photodynamic therapy. BODIPY and its derivatives as organic fluorophores have optical properties and can be used as potential sensors in various applications for biotechnological, industrial and medical purposes. In this research, a group of a new fluorescent indicators based on BODIPY structure were designed which have been composed from two seven-membered rings including Al or B atoms that has been connected with methine bridge complexed with NH2 or PH2 center. The geometries, optical properties and electronic structures of various designed molecules were studied using time-dependent density functional theory (TDDFT). The results of the calculations showed that the new designed structures are stable and highly optically active with considerable quantum yield (Φ) absorption and emission as if is promising candidates for hi-tech different applications.

Keywords

Main Subjects


[1] Z. Shoujun, Y. Qinglai, L. A Alexander, Y. Jingying, M. Zhuoran, W. Huasen, H. Wei, W. Hao, W. Joy, D. Shuo, Z. Bo, L. Xiaoyang, Z. Yeteng, Y. Kuai, H. Guosong, L. Jian, L. Yongye, D. Hongjie, PNAS., 114, 962 (2017).
[2] C. Wang, H. Tao, L. Cheng, Z. Liu, Biomaterials, 32, 6145 (2011).
[3] S.Veeranarayanan, M. Sheikh Mohamed, A. C. Poulose, M. Rinya, Y. Sakamoto, T. Maekawa, D. Sakthi Kumar, Theranostics, 8, 5231 (2018).
[4] J. Fabian, H. Nakazumi, M. Matsuoka, Chemical Reviews, 92, 1197 (1992).
[5] R. R. Lunt, V. Bulovic, Applied Physics Letters, 98, 113305 (2011).
[6] K. Kwon, T. Son, K. J. Lee, B. Jung, Lasers in Medical Science, 24, 605 (2009).
[7] A. Bera, D. Bagchi, S. K. Pal, The Journal of Physical Chemistry A., 123, 7550 (2019).
[8] Z. Shoujun, H. Zhubin, T. Rui, C.Y. Bryant, Y. Qinglai, Z. Su, O. K. Dale, N. Gang, S. Haitao, L.A. Alexander, C. Xiaoyuan, Advanced Materials, 30, 1 (2018).
[9] F. Tahmaszade, H. R. Shamlouei, Solar Energy, 188, 1031 (2019).
[11] P. Brogdon, H. Cheema, J.H. Delcamp, ChemSusChem., 11, 86 (2018).
[12] C.M. Marian, M. Etinski, V. Rai-Constapel, J. Phys. Chem. A., 118, 6985 (2014).
[13] X. Zhan, A. Facchetti, S. Barlow, T.J. Marks, M.A. Ratner, M.R. Wasielewski, S.R. Marder, Adv. Mater., 23, 268 (2011).
[14] U. Mayerhffer, K. Deing, K. Gruß, H. Braunschweig, K. Meerholz, F. Würthner, Chem. Int. Ed., 48, 8776 (2009).
[15] Z. Chen, U. Baumeister, C. Tschierske, F. Würthner, Chem. Eur. J., 13, 450 (2007).
[16] G. Fan, L. Yang and Z. Chen, Front. Chem. Sci. Eng., 8, 405 (2014).
[17] A. Loudet, K. Burgess, Chem. Rev., 107, 4891 (2007).
[18] S-C.n Lee, D. Zhai, Y-T. Chang, Tetrahedron Letters, 54, 2976 (2013).
[19] S. Zhu, J. Zhang, G. Vegesna, F-T. Luo, S.A. Green, Liu H. Org. Lett., 13, 438 (2011).
[20] N. Boens, V. Leen, W. Dehaen, F, Chem. Soc. Rev. 4, 1130 (2012).
[21] T. Kowada, H. Maeda, K. Kikuchi, Chem. Soc. Rev. 44, 4953 (2015).
[22] A. Kamkaew, SH. Lim, HB. Lee, L. Voon Kiew, LY. Chung, K. Burgess, Chem. Soc. Rev. 42, 77 (2013).
[23] SG. Awuahab, Y. You, RSC Adv. 2, 11169 (2012).
[24] W. Qin, M. Baruah, A. Stefan, M. Van der Auweraer, N. Boens, ChemPhysChem. 6, 2343 (2005).
[25] D. Frath, JE. Yarnell, G. Ulrich, FN. Castellano, R. Ziessel, ChemPhysChem. 14, 3348(2013).
[26] G. Ulrich, A. Barsella, A. Boeglin, S. Niu, R. Ziessel,
ChemPhysChem. 15, 2693 (2014).
[27] ML. Agazzi, JE. Durantini, NS. Gsponer, AM. Durantini, SG. Bertolotti, EN. Durantini,
ChemPhysChem, 20, 1110 (2019).
[28] Z-H. Pan, G-G. Luo, J-W. Zhou, J-X. Xia, K. Fang, R-B. Wu, Dalton Trans., 43, 8499 (2014).
[29] J. Kabatc, B. Jedrzejewska, A. Bajorek, and J. Paczkowski, J. Fluoresc, 16, 525 (2006).
[30] EN. Kaya, B. Köksoy, S. Yeşilot, M. Durmuş, Dyes and Pigments, 172, 107867 (2020).
[31] Y. Liu, L. Yang, C. Ma, A. Tangb, Dyes and Pigments, 173, 107981 (2020).
[32] A. Ortiz, Dyes and Pigments, 171, 107690 (2019).
[33] T. Rappitsch, I. Klimant, S.M. Borisov, Dyes and Pigments, 174, 108037 (2020).
[34] T. Xu, C. Yan, Y. Wu, C. Yuan, X. Shao, Dyes and Pigments, 168, 235 (2019).
[35] Z. Khanjari, B. Mohtat, R. Ghiasi, H. Djahaniani, F. K. Behbahani, Main Group Chemistry, 20, 59 (2021).
[36] R. Ghiasi, Z. Zandiyeh, Inorganic Chemistry Communications, 124, 108412 (2021).
[37] M. Nilchi, R. Ghiasi, E. Mohammadi Nasab. Journal of the Chilean Chemical Society, 64, 4360 (2019).
[38] P. Parsa, R. Ghiasi, A. Marjani. Inorganic Chemistry Communications, 127, 10849 (2021).
[39] M. Kiani, R. Ghiasi, H. Pasdar, B. Mirza. Russian Journal of Physical Chemistry A, 94, 345 (2020).
[40] M. Kiani, R. Ghiasi, H. Pasdar, B. Mirza. Journal of Molecular Liquids, 300, 112327 (2020).
[41] M. Laine, N. A. Barbosa, A. Kochel, B. Osiecka, G. Szewczyk, T. Sarna, P. Ziółkowski, R. Wieczorek, A. Filarowski. Sensors and Actuators B: Chemical, 238, 548 (2017).
[42] N. Shajari, R. Ghiasi, M. Soltani, A. R. Kazemizadeh, Int. J. New. Chem., 7, 283 (2020).
[43] Z. Jianzhang, K. Xu, W. Yang, Z. Wang, F. Zhong. Chemical Society Reviews, 44, 8904 (2015).
[44] V. Daneshdoost, R. Ghiasi, A. Marjani. Russian Journal of Physical Chemistry A, 94, 2594 (2020).
[45] Y. Zhao, D.G. Truhlar, Theor. Chem. Acc., 120, 215 (2006).
[46] JD. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys., 10, 6615 (2008).
[47] N.M. O'boyle, A.L. Tenderholt, K.M. Langner, J. Comput. Chem., 29, 839 (2008). [48] A. D. McLean and G. S. Chandler, J. Chem. Phys., 72, 5639 (1980). [49] K. Raghavachari, J. S. Binkley, R. Seeger, and J. A. Pople, J. Chem. Phys., 72, 650 (1980).
[50] E. Runge, EK. Gross, J. Chem. Phys., 52, 997 (1984).
[51] E. Gross, W. Kohn, Phys. Rev. Lett., 55, 2850 (1985) .
[52] ME. Casida, C. Jamorski, KC. CaBOsida, DR. Salahub, J. Chem. Phys., 108, 4439 (1998). [53] S. Azadi doureh, M. Rezaei‒Sameti, Int. J. New. Chem., 6, 109 (2019).
[54] M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comput. Chem., 24, 669 (2003).