3-/3,5-Styryl-Substituted BODIPY with N-Bridged Annulation: Synthesis and Spectroscopic Properties

Abstract

The development of organic dyes with high fluorescence quantum yield (FLQY) and tunable emission has significant application potential in biomedicine and material science. The synthesis of four N-bridged annulated BODIPY dyes with styryl units at the 3- and 3,5-positions of the BODIPY core, introduced by Knoevenagel condensation reaction, is reported. These dyes show high FLQY and tunable fluorescence. The intrinsic relationship between structure and properties is comprehensively analyzed through density functional theory (DFT) calculations, which is crucial for the rational design of new BODIPY dyes with desired properties for specific applications.

Key words

BODIPY - N-bridged annulation - Knoevenagel condensation reaction - Cadogan reaction - TD-DFT calculation

Publication History

Received: 01 October 2023

Accepted after revision: 11 December 2023

Accepted Manuscript online:
11 December 2023

Article published online:
19 January 2024

• References

• 1 Loudet A, Burgess K. Chem. Rev. 2007; 107: 4891
• 2 Bessette A, Hanan GS. Chem. Soc. Rev. 2014; 43: 3342
• 3 Lu H, Mack J, Yang Y, Shen Z. Chem. Soc. Rev. 2014; 43: 4778
• 4 Gai L, Liu Y, Zhou Z, Lu H, Guo Z. Coord. Chem. Rev. 2023; 481: 215041
• 5 Bumagina NA, Antina EV, Ksenofontov AA, Antina LA, Kalyagin AA, Berezin MB. Coord. Chem. Rev. 2022; 469: 214684
• 6 Ulrich G, Ziessel R, Harriman A. Angew. Chem. Int. Ed. 2008; 47: 1184
• 7 Bañuelos J. Chem. Rec. 2016; 16: 335
• 8 Boens N, Leen V, Dehaen W. Chem. Soc. Rev. 2012; 41: 1130
• 9 Kamkaew A, Lim SH, Lee HB, Kiew LV, Chung LY, Burgess K. Chem. Soc. Rev. 2013; 42: 77
• 10 Kowada T, Maeda H, Kikuchi K. Chem. Soc. Rev. 2015; 44: 4953
• 11 Ding C, Ren T. Coord. Chem. Rev. 2023; 482: 215080
• 12 Ehrenschwender T, Wagenknecht H.-A. Synthesis 2008; 3657
• 13 Makukhin N, Nosek V, Míšek J. Synthesis 2018; 50: 772
• 14 Wang J, Yu C, Hao E, Jiao L. Coord. Chem. Rev. 2022; 470: 214709
• 15 Ziessel R, Goze C, Ulrich G. Synthesis 2007; 936
• 16 Wu S, Gai L, Zhou Z, Lu H. Org. Chem. Front. 2022; 9: 5989
• 17 Đorđević L, Milano D, Demitri N, Bonifazi D. Org. Lett. 2020; 22: 4283
• 18 Manjare ST, Kim J, Lee Y, Churchill DG. Org. Lett. 2014; 16: 520
• 19 Feng S, Qu Z, Zhou Z, Chen J, Gai L, Lu H. Chem. Commun. 2021; 57: 11689
• 20 Wu Y, Mack J, Xiao X, Li Z, Shen Z, Lu H. Chem. Asian J. 2017; 12: 2216
• 21 Bunyan PJ, Cadogan JI. G. J. Chem. Soc. 1963; 42
• 22 Cadogan JI. G, Cameron-Wood M, Mackie RK, Searle RJ. G. J. Chem. Soc. 1965; 4831
• 23 Sun Y, Yuan H, Di L, Zhou Z, Gai L, Xiao X.-Q, He W, Lu H. Org. Chem. Front. 2019; 6: 3961
• 24 Gai L, Mack J, Lu H, Yamada H, Kuzuhara D, Lai G, Li Z, Shen Z. Chem. Eur. J. 2014; 20: 1091
• 25 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16, Revision C.01 . Gaussian, Inc; Wallingford CT: 2016