Citation: Jie Zhou, Manna Huang, Xinhai Zhu, Yiqian Wan. One-pot synthesis of dual-state emission (DSE) luminogens containing the V-shape furo[2, 3-b]furan scaffold[J]. Chinese Chemical Letters, ;2021, 32(1): 445-448. doi: 10.1016/j.cclet.2020.02.038 shu

One-pot synthesis of dual-state emission (DSE) luminogens containing the V-shape furo[2, 3-b]furan scaffold

Jie Zhou ^{a, 1} ,
Manna Huang ^{a, *} ,
Xinhai Zhu ^b ,
Yiqian Wan ^{a, *}

a.
School of Chemical Engineering and Technology, Guangdong Engineering Technology Research Center for Platform Chemicals from Marine Biomass and Their Functionalization, Sun Yat-sen University, Zhuhai 519082, China
b.
Instrument Analysis & Research Center, Sun Yat-sen University, Guangzhou 510275, China

huangmn25@mail.sysu.edu.cn

ceswyq@mail.sysu.edu.cn

Received Date: 8 January 2020
Revised Date: 11 February 2020
Accepted Date: 20 February 2020
Available Online: 21 February 2020

Figures(4)

To discover novel fluorophores of solution and solid dual-state emission (DSE) materials, unique V-shape furo[2, 3-b]furans have been designed and synthesized by a one-pot method for the first time and their photoluminescent properties have been explored in benzene, THF, DMF and DMSO, as well as in the solid state. As the best example, 2, 5-bis(4-(9H-carbazol-9-yl)phenyl)-6a-amino-3a, 6a-dihydrofuro[2, 3-b] furan-3, 3a, 4-tricarbonitrile (3g) exhibited solution and solid DSE properties in THF, benzene, and in the solid state with quantum yields of 55%, 92%, and 45%, respectively.
- One-pot synthesis,
- Furo[2, 3-b]furan,
- Selenium dioxide,
- V-Shape,
- Dual-state emission
1. [1]
  (a) B. valeur, M.N. Berberan-Santos, Molecular Fluorescence-Principles and Applications, 2nd ed., Wiley-VCH Verlag & Co., Weinheim, 2012;
  (b) A.S. Klymchenko, Acc. Chem. Res. 50 (2017) 366-375;
  (c) V.M. Alexander, P.L. Choyke, H. Kobayashi, Curr. Mol. Med. 13 (2013) 1568-1578;
  (d) S. Mizukami, H. Houjou, K. Sugaya, et al., Chem. Mater. 17 (2005) 50-56;
  (e) S.C.F. Kui, S.S.Y. Chui, C.M. Che, N. Zhu, J. Am. Chem. Soc. 128 (2006) 8297-8309.
2. [2]
  (a) T. Qin, W. Wiedemair, S. Nau, et al., J. Am. Chem. Soc. 133 (2011) 1301-1303;
  (b) L. Duan, J. Qiao, Y. Sun, Y. Qiu, Adv. Mater. 23 (2011) 1137-1144;
  (c) A.C. Grimsdale, K.L. Chan, R.E. Martin, P.G. Jokisz, A.B. Holmes, Chem. Rev. 109 (2009) 897-1091;
  (d) R.H. Friend, R.W. Gymer, A.B. Holmes, et al., Nature 397 (1999) 121-128;
  (e) T. Khanasa, N. Prachumrak, R. Rattanawan, et al., J. Org. Chem. 78 (2013) 6702-6713.
3. [3]
  (a) J. Zhang, W. Chen, A.J. Rojas, et al., J. Am. Chem. Soc. 135 (2013) 16376-16379;
  (b) H. Lu, C. Zhang, G. Xia, et al., RSC Adv. 6 (2016) 96196-96201.
4. [4]
  (a) T. Weil, T. Vosch, J. Hofkens, K. Peneva, K. Mullen, Angew. Chem. Int. Ed. 49 (2010) 9068-9093;
  (b) T. Mutai, T. Ohkawa, H. Shono, K. Araki, J. Mater. Chem. C 4 (2016) 3599-3606.
5. [5]
  (a) Z. Zhang, B. Xu, J. Su, et al., Angew. Chem. Int. Ed. 50 (2011) 11654-11657;
  (b) B.K. An, S.K. Kwon, S.D. Jung, S.Y. Park, J. Am. Chem. Soc. 124 (2002) 14410-14415;
  (c) J. Luo, Z. Xie, J.W. Y. Lam, et al., Chem. Commun. (2001) 1740-1741;
  (d) S.P. Anthony, ChemPlusChem 77 (2012) 518-531.
6. [6]
  (a) X. You, G. Zhang, C. Zhan, Y. Wang, D. Zhang, ACS Symp. Ser. 1227 (2016) 93-127;
  (b) C. Zhan, X. You, G. Zhang, et al., Chem. Rec. 16 (2016) 2142-2160.
7. [7]
  D. Mao, D. Ding, ACS Symp. Ser. 1227 (2016) 217-243.
8. [8]
  (a) S.H. Bae, K.D. Seo, W.S. Choi, J.Y. Hong, H.K. Kim, Dyes Pigm. 113 (2015) 18-26;
  (b) N. Manfredi, B. Cecconi, A. Abbotto, Eur. J. Org. Chem. 2014 (2014) 7069-7086.
9. [9]
  Z. Chi, J. Xu, Mechanochromic Aggregation-Induced Emission Materials in Aggregation-Induced Emiss. Appl, John Wiley & Sons, Ltd, 2013, pp. 61-86.
10. [10]
  (a) X. Sun, Y. Wang, Y. Lei, Chem. Soc. Rev. 44 (2015) 8019-8061;
  (b) J.L. Banal, B. Zhang, D.J. Jones, K.P. Ghiggino, W.W. H. Wong, Acc. Chem. Res. 50 (2017) 49-57;
  (c) Y. Yuan, B. Liu, Chem. Sci. 8 (2017) 2537-2546;
  (d) X. Gu, T.K. Kwok Ryan, W.Y. Lam Jacky, B.Z. Tang, Biomaterials 146 (2017) 115-135;
  (e) Y. Hong, W.Y. Lam Jacky, B.Z. Tang, Chem. Soc. Rev. 40 (2011) 5361-5388;
  (f) T.K. Kwok Ryan, W.T. Leung Chris, W.Y. Lam Jacky, B.Z. Tang, Chem. Soc. Rev. 44 (2015) 4228-4238;
  (g) P. Zhao, L. Zhu, Chin. Chem. Lett. 29 (2018) 1706-1708.
11. [11]
  G. Chen, W. Li, T. Zhou, et al., Adv. Mater. 27 (2015) 4496-4501. doi: 10.1002/adma.201501981
12. [12]
  B. Chen, G. Yu, X. Li, et al., J. Mater. Chem. C 1 (2013) 7409-7417. doi: 10.1039/c3tc31751j
13. [13]
  (a) T. Beppu, K. Tomiguchi, A. Masuhara, Y.J. Pu, H. Katagiri, Angew. Chem. Int. Ed. 54 (2015) 7332-7335;
  (b) A. Patra, S.P. Anthony, T.P. Radhakrishnan, Adv. Funct. Mater. 17 (2007) 2077-2084;
  (c) S. Kumar, P. Singh, P. Kumar, et al., J. Phys. Chem. C 120 (2016) 12723-12733;
  (d) H. Wu, Z. Chen, W. Chi, et al., Angew. Chem. Int. Ed. 58 (2019) 11419-11423.
14. [14]
  (a) D.K. You, J.H. Lee, B.H. Choi, et al., Eur. J. Inorg. Chem. 2017 (2017) 2496-2503;
  (b) A. Raghuvanshi, A.K. Jha, A. Sharma, et al., Chem. Eur. J. 23 (2017) 4527-4531;
  (c) H. Naito, K. Nishino, Y. Morisaki, K. Tanaka, Y. Chujo, Angew. Chem. Int. Ed. 56 (2017) 254-259;
  (d) P. Gopikrishna, P.K. Iyer, J. Phys. Chem. C 120 (2016) 26556-26568.
15. [15]
  A. C. Shaikh, D.S. Ranade, S. Thorat, et al., Chem. Commun. 51 (2015) 16115-16118. doi: 10.1039/C5CC06351E
16. [16]
  H. Yamane, K. Tanaka, Y. Chujo, Tetrahedron Lett. 56 (2015) 6786-6790. doi: 10.1016/j.tetlet.2015.10.072
17. [17]
  (a) M. Huang, S. Ye, K. Xu, et al., J. Mater. Chem. C 5 (2017) 3456-3460;
  (b) E. Heyer, J. Massue, G. Ulrich, Dyes Pigm. 143 (2017) 18-24;
  (c) E. Heyer, K. Benelhadj, S. Budzak, et al., Chem. Eur. J. 23 (2017) 7324-7336.
18. [18]
  (a) P. Vila-Donat, S. Marin, V. Sanchis, A.J. Ramos, Food Chem. Toxicol. 114 (2018) 246-259;
  (b) Y. Hayashi, T. Aikawa, Y. Shimasaki, et al., Org. Process Res. Dev. 20 (2016) 1615-1620;
  (c) G.L. Moore, R.W. Stringham, D.S. Teager, T.Y. Yue, Org. Process Res. Dev. 21 (2017) 98-106.
19. [19]
  V. J. Aran, N. Martin, C. Seoane, J.L. Soto, J. Sanz-Aparicio, F. Florencio, J. Org. Chem. 53 (1988) 5341-5343. doi: 10.1021/jo00257a025
20. [20]
  (a) G. Sathiyan, P. Sakthivel, Dyes Pigm. 143 (2017) 444-454;
  (b) G. Gopan, P.S. Salini, S. Deb, M. Hariharan, CrystEngComm 19 (2017) 419-425;
  (c) W.Y. Wong, S.F. Lee, H.S. Chan, et al., RSC Adv. 3 (2013) 26382-26390;
  (d) S. Sekiguchi, K. Kondo, Y. Sei, M. Akita, M. Yoshizawa, Angew. Chem. Int. Ed. 55 (2016) 6906-6910.
21. [21]
  J. Zhou, X. Zhu, M. Huang, Y. Wan, Eur. J. Org. Chem. 2017 (2017) 2317-2321. doi: 10.1002/ejoc.201700383
22. [22]
  H. Tong, Y. Hong, Y. Dong, et al., J. Phys. Chem. B 111 (2007) 2000-2007. doi: 10.1021/jp067374k
1. [1]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
2. [2]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
3. [3]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
4. [4]
  Yaping Wang , Pengcheng Yuan , Zeyuan Xu , Xiong-Xiong Liu , Shengfa Feng , Mufan Cao , Chen Cao , Xiaoqiang Wang , Long Pan , Zheng-Ming Sun . Ti₃C₂T_x MXene in-situ transformed Li₂TiO₃ interface layer enabling 4.5 V-LiCoO₂/sulfide all-solid-state lithium batteries with superior rate capability and cyclability. Chinese Chemical Letters, 2024, 35(6): 108776-. doi: 10.1016/j.cclet.2023.108776
5. [5]
  Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg²⁺/B³⁺ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722
6. [6]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
7. [7]
  Mengxiang Zhu , Tao Ding , Yunzhang Li , Yuanjie Peng , Ruiping Liu , Quan Zou , Leilei Yang , Shenglei Sun , Pin Zhou , Guosheng Shi , Dongting Yue . Graphene controlled solid-state growth of oxygen vacancies riched V₂O₅ catalyst to highly activate Fenton-like reaction. Chinese Chemical Letters, 2024, 35(12): 109833-. doi: 10.1016/j.cclet.2024.109833
8. [8]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
9. [9]
  Xi Tang , Chunlei Zhu , Yulu Yang , Shihan Qi , Mengqiu Cai , Abdullah N. Alodhayb , Jianmin Ma . Additive regulating Li⁺ solvation structure to construct dual LiF−rich electrode electrolyte interphases for sustaining 4.6 V Li||LiCoO₂ batteries. Chinese Chemical Letters, 2024, 35(12): 110014-. doi: 10.1016/j.cclet.2024.110014
10. [10]
  Lanfang Wang , Jiangnan Lv , Yujia Li , Yanqing Hao , Wenjiao Liu , Hui Zhang , Xiaohong Xu . One-step synthesis of nanowoven ball-like NiS-WS₂ for high-efficiency hydrogen evolution. Chinese Chemical Letters, 2025, 36(1): 109597-. doi: 10.1016/j.cclet.2024.109597
11. [11]
  Xiao Xiao , Biao Chen , Jia-Wei Li , Jun-Bo Zheng , Xu Wang , Hang Zhao , Fen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280
12. [12]
  Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt₃M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188
13. [13]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
14. [14]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
15. [15]
  Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
16. [16]
  Xingxing Jiang , Yuxin Zhao , Yan Kong , Jianju Sun , Shangzhao Feng , Xin Lu , Qi Hu , Hengpan Yang , Chuanxin He . Support effect and confinement effect of porous carbon loaded tin dioxide nanoparticles in high-performance CO₂ electroreduction towards formate. Chinese Chemical Letters, 2025, 36(1): 109555-. doi: 10.1016/j.cclet.2024.109555
17. [17]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
18. [18]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
19. [19]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
20. [20]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(935)
HTML views(174)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142