Novel AIEEgens: Small Structure Modification with Significant Property Change

Abstract

In this study, a series of small molecules based on 3-(dimethylamino)-1-(2-hydroxyphenyl)-2-propen-1-one have been prepared under mild reaction conditions. Most of the compounds showed high fluorescence quantum yield in the solid-state (Φ_Fmax = 0.75). In addition, the fluorescence emission color was effectively and simply changed by modifying the substituent on the aromatic ring. The crystalline state and the photophysical properties of all the compounds in THF(DMF)/water mixtures were investigated, exhibiting marked aggregation-induced enhanced emission characteristics. The X-ray crystallographic analysis explained the different emissions of these compounds.

Key words

AIEE - solid-state fluorescence - color-tunable-emission - small molecules - high fluorescence quantum yield

Publication History

Received: 31 October 2024

Accepted after revision: 16 January 2025

Accepted Manuscript online:
16 January 2025

Article published online:
06 March 2025

• References

• 1 D’Andrade B. Nat. Photonics 2007; 1: 33
• 2 Pfeiffer M, Forrest SR, Leo K, Thompson ME. Adv. Mater. 2002; 14: 1633
• 3 Kena-Cohen S, Forrest SR. Nat. Photonics 2010; 4: 371
• 4 Luo J, Xie Z, Lam JW. Y, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Chem. Commun. 2001; 1740
• 5 An B, Kwon S, Jung S, Park SY. J. Am. Chem. Soc. 2002; 124: 14410
• 6 Tong X, Zhao Y, An B.-K, Park SY. Adv. Funct. Mater. 2006; 16: 1799
• 7a Xue W, Zhang G, Zhang D, Zhu D. Org. Lett. 2010; 12: 2274
• 7b Hu R, Feng J, Hu D, Wang S, Li S, Li Y, Yang G. Angew. Chem. Int. Ed. 2010; 49: 4915
• 7c Hong Y, Lam JW. Y, Tang BZ. Chem. Commun. 2009; 4332
• 7d Noh SB, Kim RH, Kim WJ, Kim S, Lee K.-S, Cho NS, Shim H.-K, Pudavar HE, Prasad PN. J. Mater. Chem. 2010; 20: 7422
• 7e Wang M, Zhang D, Zhang G, Zhu D. Chem. Commun. 2008; 37: 4469
• 8a Yu G, Yin S, Liu Y, Shuai Z, Zhu D. J. Am. Chem. Soc. 2003; 125: 14816
• 8b Ning Z, Chen Z, Zhang Q, Yan Y, Qian S, Cao Y, Tian H. Adv. Funct. Mater. 2007; 17: 3799
• 9a Zhang X, Zhang X, Tao L, Chi Z, Xu J, Wei Y. J. Mater. Chem. B 2014; 2: 4398
• 9b Ding D, Li K, Liu B, Tang BZ. Acc. Chem. Res. 2013; 46: 2441
• 9c Mei J, Wang J, Sun JZ, Zhao H, Yuan W, Deng C, Chen S, Sung HH. Y, Lu P, Qin A, Kwok HS, Ma Y, Williams ID, Tang BZ. Chem. Sci. 2012; 3: 549
• 9d Huang J, Sun N, Chen P, Tang R, Li Q, Ma D, Li Z. Chem. Commun. 2014; 50: 2136
• 10a Liu J, Zhong Y, Lam JW. Y, Lu P, Hong Y, Yu Y, Yue Y, Faisal M, Sung HH. Y, Williams ID, Wong KS, Tang BZ. Macromolecules 2010; 43: 4921
• 10b Zhang X, Chi Z, Li H, Xu B, Li X, Liu S, Zhang Y, Xu J. J. Mater. Chem. 2011; 21: 1788
• 10c Luo J, Xie Z, Lam JW. Y, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Chem. Commun. 2001; 1740
• 10d Chen M, Li L, Nie H, Tong J, Yan L, Xu B, Sun JZ, Tian W, Zhao Z, Qin A, Tang BZ. Chem. Sci. 2015; 6: 1932
• 10e Chen L, Jiang Y, Nie H, Lu P, Sung HH. Y, Williams ID, Kwok HS, Huang F, Qin A, Zhao Z, Tang BZ. Adv. Funct. Mater. 2014; 24: 3621
• 10f Zhang X, Chi Z, Zhou X, Liu S, Zhang Y, Xu J. J. Phys. Chem. C 2012; 116: 23629
• 10g Zhang X, Chi Z, Xu B, Jiang L, Zhou X, Zhang Y, Liu S, Xu J. Chem. Commun. 2012; 48: 10895
• 10h Gu X, Yao J, Zhang G, Zhang C, Yan Y, Zhao Y, Zhang D. Chem. Asian J. 2013; 8: 2362
• 11a Huang M, Yu R, Xu K, Ye S, Kuang S, Zhu X, Wan Y. Chem. Sci. 2016; 7: 4485
• 11b Mi S, Wu J, Liu J, Xu Z, Wu X, Luo G, Zheng J, Xu C. ACS Appl. Mater. Interfaces 2015; 7: 27511
• 11c Jadhav T, Choi JM, Dhokale B, Mobin SM, Lee JY, Misra R. J. Phys. Chem. C 2016; 120: 18487
• 11d Han F, Zhang R, Zhang Z, Su J, Ni Z. RSC Adv. 2016; 6: 68178
• 11e Chen J, Law CC. W, Lam JW. Y, Dong Y, Lo SM. F, Williams ID, Zhu D, Tang BZ. Chem. Mater. 2003; 15: 1535
• 12a Beppu T, Tomiguchi K, Masuhara A, Pu Y.-J, Katagiri H. Angew. Chem. Int. Ed. 2015; 54: 7332
• 12b Li Z.-Y, Liu F, Li H, Guo X, Jiao L, Hao E. Org. Lett. 2024; 26: 444
• 13a Biegasiewicz KF, Gordon JS, Rodriguez DA, Priefer R. Tetrahedron Lett. 2014; 55: 5210
• 13b Li G, Zhang Z.-T, Dai L.-Y, Du Y.-L, Xue D. Helv. Chim. Acta 2012; 95: 989
• 13c Zhang X.-Z, Ge D.-L, Chen S.-Y, Yu X.-Q. RSC Adv. 2016; 6: 66320
• 13d Levchenko KS, Semenova IS, Yarovenko VN, Shmelin PS, Krayushkin MM. Tetrahedron Lett. 2012; 53: 3630
• 14 Yin P.-A, Ou Q, Peng Q, Shuai Z. Aggregate 2023; 4: e291
• 15 Horvath P, Sebej P, Solomek T, Klan P. J. Org. Chem. 2015; 80: 1299
• 16 Araneda JF, Piers WE, Heyne B, Parvez M, McDonald R. Angew. Chem. Int. Ed. 2011; 50: 12214
• 17 Schill H, Nizamov S, Bottanelli F, Bierwagen J, Belov VN, Hell SW. Chem. Eur. J. 2013; 19: 16556
• 18 Wu Y, Chen Y, Gou G, Mu W, Lv X, Du M, Fu W. Org. Lett. 2012; 14: 5226
• 19 Zhang X, Chi Z, Xu B, Chen C, Zhou X, Zhang Y, Liu S, Xu J. J. Mater. Chem. 2012; 22: 18505
• 20a Yang Z, Chi Z, Xu B, Li H, Zhang X, Li X, Liu S, Zhang Y, Xu J. J. Mater. Chem. 2010; 20: 7352
• 20b Dong S, Li Z, Qin J. J. Phys. Chem. B 2009; 113: 434
• 20c Yang Z, Chi Z, Yu T, Zhang X, Chen M, Xu B, Liu S, Zhang Y, Xu J. J. Mater. Chem. 2009; 19: 5541
• 21a Yang J, Ren Z, Chen B, Fang M, Zhao Z, Tang BZ, Peng Q, Li Z. J. Mater. Chem. C 2017; 5: 9242
• 21b Liu H, Yao L, Li B, Chen X, Gao Y, Zhang S, Li W, Lu P, Yang B, Ma Y. Chem. Commun. 2016; 52: 7356
• 21c Hisamatsu S, Masu H, Takahashi M, Kishikawa K, Kohmoto S. Cryst. Growth Des. 2015; 15: 2291
• 21d Hinoue T, Shigenoi Y, Sugino M, Mizobe Y, Hisaki I, Miyata M, Tohnai N. Chem. Eur. J. 2012; 18: 4634
• 21e Yang W, Liu C, Lu S, Du J, Gao Q, Zhang R, Liu Y, Yang C. J. Mater. Chem. C 2018; 6: 290
• 21f Padalkar VS, Sakamaki D, Kuwada K, Horio A, Okamoto H, Tohnai N, Akutagawa T, Sakai K.-i, Seki S. Asian J. Org. Chem. 2016; 5: 938
• 21g Rajagopal SK, Philip AM, Nagarajan K, Hariharan M. Chem. Commun. 2014; 50: 8644
• 22a Liu Y, Tao X, Wang F, Shi J, Sun J, Yu W, Ren Y, Zou D, Jiang M. J. Phys. Chem. C 2007; 111: 6544
• 22b Cheng X, Wang K, Huang S, Zhang H, Zhang H, Wang Y. Angew. Chem. Int. Ed. 2015; 54: 8369