Citation: LI Tian-Tian, Yuan YUAN, ZHOU An-Nan, XU Qing-Hong. A π-Conjugated Organic Molecule: BDOBC16 Assembly in Silylated SBA-15 and Luminescent Properties[J]. Chinese Journal of Inorganic Chemistry, ;2016, 32(3): 508-516. doi: 10.11862/CJIC.2016.067 shu

A π-Conjugated Organic Molecule: BDOBC16 Assembly in Silylated SBA-15 and Luminescent Properties

1.
State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China
2.
Petrochemical Research Institute, PetroChina Company Limited, Beijing 100083, China

Corresponding author: XU Qing-Hong,
Received Date: 13 September 2015
Revised Date: 14 January 2016

Figures(12)

4, 4-(9-(n-Hexadecyl) carbazole-3, 6-diyl) di (6-(4-(diphenylamino) phenyl)-2, 2-difluoro-1, 3, 2(2H)-diox-aborine) (named as BDOBC16), a kind of π-conjugated organic molecule containing β-diketone-boron difluoride groups, was assembled in SBA-15 modified with (3-aminopropyl) triethoxysilane (APTES), and fluorine-boron groups in molecule of BDOBC16 was found to be remained in the assembly. Results indicate that the organic compound in silylated SBA-15 emits green light while itself emits red light. The energy of 0.45 eV is found changeable in emission of the guest before and after assembly, and luminescent intensity of BDOBC16 increases 75 times after it was assembled. Strong H-bond existed between the host and the guest, which is regarded as main reason to result tremendous change in luminescence of the guest. Molecular aggregation is also found harmful while high dispersion is benefit to luminescence of the guest.
- conjugation,
- mesoporous material,
- silicates,
- self-assembly,
- luminescence
1. [1]
  Saito K, Kuwabara J, Kanbara T. Synth. Met., 2011, 161: 1150-1153 doi: 10.1016/j.synthmet.2011.02.019
2. [2]
  Park Y, Advincula R C. Chem. Mater., 2011, 23:4273-4294 doi: 10.1021/cm201199u
3. [3]
  Cai J, Niu H, Wang C, et al. Electrochim. Acta, 2012, 76: 229-241 doi: 10.1016/j.electacta.2012.04.117
4. [4]
  Rochat S, Swager T M. ACS Appl. Mater. Interfaces, 2013, 5: 4488-4502 doi: 10.1021/am400939w
5. [5]
  Zhou Y, Kim J W, Yoon J. Organ. Lett., 2010, 12:1272-1275 doi: 10.1021/ol100160d
6. [6]
  Ripaud E, Demeter D, Leriche P, et al. Dyes Pigm., 2012, 95:126-133 doi: 10.1016/j.dyepig.2012.03.021
7. [7]
  Liu X, Zhang X, Lu R. J. Mater. Chem., 2011, 21:8756-8765 doi: 10.1039/c0jm04274a
8. [8]
  Elson E L. Biophys. J., 2011:2855-2870
9. [9]
  Zhao C H, Wakamiya A, Inukai Y, et al. J. Am. Chem. Soc., 2006, 128:15934-15935 doi: 10.1021/ja0637550
10. [10]
  Li W, Li Q, Huang L Y F. Dyes Pigm., 2015, 113:1-7 doi: 10.1016/j.dyepig.2014.07.034
11. [11]
  Thomas Ⅲ S W, Joly G D, Swager T M. Chem. Rev., 2007, 107:1339-1386 doi: 10.1021/cr0501339
12. [12]
  Zhao Z, Lu P, Tang B Z. Chem. Sci., 2011, 2:672-675 doi: 10.1039/C0SC00521E
13. [13]
  Chiang C L, Chen C T, Hsu C P, et al. Adv. Funct. Mater., 2008, 18:248-257 doi: 10.1002/(ISSN)1616-3028
14. [14]
  Liu J, Lam J W Y, Tang B Z. Chem. Rev., 2009, 109:5799-5867 doi: 10.1021/cr900149d
15. [15]
  Fan H, Hu Q D, Xu F J, et al. Biomaterials, 2012, 33:1428-1436 doi: 10.1016/j.biomaterials.2011.10.043
16. [16]
  Fujita M, Tominaga M, Hori A, et al. Acc. Chem. Res., 2005, 38:369-378 doi: 10.1021/ar040153h
17. [17]
  Shi W J, Menting R, Ng D K P. Chem. Commun., 2013, 49: 5277 doi: 10.1039/c3cc00095h
18. [18]
  Muraoka T, Kinbara K, Aida T. Nature, 2006:440
19. [19]
  Wang L, Lei J, Ma R, et al. Anal. Chem., 2013, 85:6505-6510 doi: 10.1021/ac401105p
20. [20]
  Agasti S S, Liong M, Lee H, et al. Angew. Chem. Int. Ed., 2012, 51:450-454 doi: 10.1002/anie.201105670
21. [21]
  Hu J, Liu S. Chem. Mater., 2011, 23:1088-1090 doi: 10.1021/cm103216a
22. [22]
  Hu J, Liu S. Acc. Chem. Res., 2014, 47:2084-2095 doi: 10.1021/ar5001007
23. [23]
  Chan M Y, Lai S L, Lee C S. Adv. Funct. Mater., 2007, 17: 2509-2514 doi: 10.1002/(ISSN)1616-3028
24. [24]
  Schenning A P H J, Meijer E W. Chem. Commun., 2005: 3245
25. [25]
  Zhou Y, Xiao Y, Li D, et al. J. Org. Chem., 2008, 73:1571-1574 doi: 10.1021/jo702265x
26. [26]
  Nandi M, Mondal J, Yamauchic Y, et al. Chem. Commun., 2011, 47:6677-6679 doi: 10.1039/c1cc11007a
27. [27]
  Zhao D Y, Feng J L, Huo Q, et al. Science, 1998, 279:548 doi: 10.1126/science.279.5350.548
28. [28]
  Zhao D Y, Yang P D, Melosh N, et al. Adv. Mater., 1998, 10 (16):1380-1385 doi: 10.1002/(ISSN)1521-4095
29. [29]
  Mondal J, Borah P, Bhaumik A. Org. Process Res. Dev., 2014, 18:257-265 doi: 10.1021/op4000994
30. [30]
  Ma R Z, Yao Q C, Yang X, et al. J. Fluorine Chem., 2012, 137:93-98 doi: 10.1016/j.jfluchem.2012.03.006
31. [31]
  Xu Q, Li L, Liu X, et al. Chem. Mater., 2002, 14(2):549-555 doi: 10.1021/cm0102234
1. [1]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
2. [2]
  Ting WANG , Peipei ZHANG , Shuqin LIU , Ruihong WANG , Jianjun ZHANG . A Bi-CP-based solid-state thin-film sensor: Preparation and luminescence sensing for bioamine vapors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1615-1621. doi: 10.11862/CJIC.20240134
3. [3]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
4. [4]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
5. [5]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
6. [6]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
7. [7]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
8. [8]
  Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
9. [9]
  Hao Zhang , Hao Liu , Ke Huang , Qingxiu Xia , Hongjie Xiong , Xiaohui Liu , Hui Jiang , Xuemei Wang . Ionic exchange based intracellular self-assembly of pitaya-structured nanoparticles for tumor imaging. Chinese Chemical Letters, 2025, 36(6): 110281-. doi: 10.1016/j.cclet.2024.110281
10. [10]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
11. [11]
  Yan Cheng , Hua-Peng Ruan , Yan Peng , Longhe Li , Zhenqiang Xie , Lang Liu , Shiyong Zhang , Hengyun Ye , Zhao-Bo Hu . Magnetic, dielectric and luminescence synergetic switchable effects in molecular material [Et₃NCH₂Cl]₂[MnBr₄]. Chinese Chemical Letters, 2024, 35(4): 108554-. doi: 10.1016/j.cclet.2023.108554
12. [12]
  Kai An , Qinglong Qiao , Lovelesh , Syed Ali Abbas Abedi , Xiaogang Liu , Zhaochao Xu . "Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization. Chinese Chemical Letters, 2025, 36(1): 109786-. doi: 10.1016/j.cclet.2024.109786
13. [13]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
14. [14]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
15. [15]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
16. [16]
  Siyu Zong , Xiaowei Yu , Yining Yang , Xin Yang , Jiyang Li . Multi-mode luminescence anti-counterfeiting and visual iron(Ⅲ) ions RTP detection constructed by assembly of CDs&Eu³⁺ in porous RHO zeolite. Chinese Chemical Letters, 2025, 36(6): 110343-. doi: 10.1016/j.cclet.2024.110343
17. [17]
  Yujuan Zhao , Zaiwang Zhao . Monolayer mesoporous nanosheets with surface asymmetry via a dual-emulsion-directed monomicelle assembly. Chinese Journal of Structural Chemistry, 2024, 43(2): 100238-100238. doi: 10.1016/j.cjsc.2024.100238
18. [18]
  Xiaonan LI , Hui HAN , Yihan ZHANG , Jing XIONG , Tingting GUO , Juanzhi YAN . A viologen‐based Cd(Ⅱ) coordination polymer: Self‐assembly, thermochromism, and electrochemical property. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1439-1444. doi: 10.11862/CJIC.20240376
19. [19]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
20. [20]
  Huijie An , Chen Yang , Zhihui Jiang , Junjie Yuan , Zhongming Qiu , Longhao Chen , Xin Chen , Mutu Huang , Linlang Huang , Hongju Lin , Biao Cheng , Hongjiang Liu , Zhiqiang Yu . Luminescence-activated Pt(Ⅳ) prodrug for in situ triggerable cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109134-. doi: 10.1016/j.cclet.2023.109134

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(598)
HTML views(95)

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