Shape-Persistent pi-Conjugated Macrocycles with Aggregation-Induced Emission Property: Synthesis, Mechanofluorochromism, and Mercury(II) Detection

Liu, Yi1,3; Lin, Fa Xu2; Feng, Yang1; Liu, Xiaoqing4; Wang, Lei1; Yu, Zhen-Qiang2,3; Tang, Ben Zhong5

2019-09-18

10.1021/acsami.9b10702

ACS Applied Materials & Interfaces   影响因子和分区

1944-8244

1944-8252

Shape-persistent conjugated macrocycles are fundamentally important because of their unique structure and properties. Herein, a series of pi-conjugated macrocycles with a shape-persistent architecture, an adaptive backbone, and aggregation-induced emission (AIE) properties are synthesized via oxidative coupling of acetylene-terminated tetraphenylethylene precursor with a half-ring topology and following transformation from butadiynylene linkers into thienylene ones. Characterization by NMR spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry provided unambiguous proofs for the macrocyclic structures. In particular, the free rotation of aromatic rings in the rigid macrocyclic backbone was validated by two-dimensional NMR spectroscopy, variable-temperature NMR measurements, and theoretical calculations. Moreover, these shape-persistent macrocyclic chromophores all exhibited obvious AIE phenomena and remarkable mechanofluorochromism behaviors with a red-shifted luminescence upon grinding and blue-shifted emission after solvent annealing. Also, the introduction of S atoms into the macrocyclic frameworks endowed the macrocyclic luminogen the capability to selectively detect mecury(II) ions in aqueous media among other metal ions.

Shape-persistent macrocycles porous luminogens aggregation-induced emission mechanofluorochromism mercury(II) sensor

SCI ; EI

英语

其他

Shenzhen University[2018005]

Science & Technology - Other Topics ; Materials Science

Nanoscience & Nanotechnology ; Materials Science, Multidisciplinary

WOS:000487179900077

AMER CHEMICAL SOC

20194007483836

Chromophores ; Mass spectrometry ; Mercury compounds ; Metal ions ; Metals ; Red Shift

Metallurgy:531.1 ; Light/Optics:741.1 ; Chemistry:801 ; Organic Compounds:804.1

Web of Science

1.Shenzhen Univ, Shenzhen Key Lab Polymer Sci & Technol, Guangdong Res Ctr Interfacial Engn Funct Mat, Coll Mat Sci & Engn, Shenzhen 518060, Peoples R China
2.Shenzhen Univ, Sch Chem & Environm Engn, Shenzhen 518060, Peoples R China
3.Shenzhen Univ, Ctr AIE Res, Shenzhen 518060, Peoples R China
4.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518005, Peoples R China
5.HKUST Shenzhen Res Inst, 9 Yuexing 1st Rd,South Area,Hitech Pk Nanshan, Shenzhen 518057, Peoples R China

Liu, Yi,Lin, Fa Xu,Feng, Yang,et al. Shape-Persistent pi-Conjugated Macrocycles with Aggregation-Induced Emission Property: Synthesis, Mechanofluorochromism, and Mercury(II) Detection[J]. ACS Applied Materials & Interfaces,2019,11(37):34232-34240.

Liu, Yi.,Lin, Fa Xu.,Feng, Yang.,Liu, Xiaoqing.,Wang, Lei.,...&Tang, Ben Zhong.(2019).Shape-Persistent pi-Conjugated Macrocycles with Aggregation-Induced Emission Property: Synthesis, Mechanofluorochromism, and Mercury(II) Detection.ACS Applied Materials & Interfaces,11(37),34232-34240.

Liu, Yi,et al."Shape-Persistent pi-Conjugated Macrocycles with Aggregation-Induced Emission Property: Synthesis, Mechanofluorochromism, and Mercury(II) Detection".ACS Applied Materials & Interfaces 11.37(2019):34232-34240.