Two Cholesterol-Containing Pyrene Derivatives: Subtle Spacer Difference, Diverse Stimuli-Responsive Luminescence, Chirality, and Self-Assembly Behaviors

Zhang，Hongyan1; Chang，Xiaoyong2; Ma，Chaoyang1; Huang，Guangxi1; Li，Bing Shi1; Tang，Ben Zhong3

2022-09-28

10.1021/acsami.2c12224

ACS Applied Materials & Interfaces   Impact Factor & Quartile

1944-8244

1944-8252

Two chiral molecules 1 and 2 were designed and synthesized with a pyrene moiety directly linked to a chiral cholesterol moiety and connected through a methylene spacer, respectively. Influence of the spacer on their stimuli-responsive luminescence, chirality, and self-assembly behaviors was systematically investigated. Molecules 1 and 2 had similar aggregation-induced emission enhancement (AIEE) in solution, because of carrying the same fluorescence moiety. Both molecules displayed mechanochromism (MC) property but with different color contrast, whereas only 2 showed mechanoluminescence (ML) activity. When doping in liquid crystal molecule 5CB, both molecules induced the formation of chiral nematic liquid crystals (N*-LCs) with strong circularly polarized luminescence (CPL). Molecule 2 induced single handedness signal, irrespective of doping ratios, while 1-doped N*-LCs showed an inversion of CPL signal from negative to positive upon the increase of doping ratios. Molecules 1 and 2 also self-assembled into different coassemblies with 5CB. Their distinct behaviors were attributed to the influence of the methylene spacer, which caused different molecular conformation and steric bulkiness; accordingly, it changed intermolecular interactions and molecular packing of the two molecules and led to diverse chirality and luminescence. This work provided important model molecules to better understand the molecular structure-property relationship and guide the design of novel functional molecules.

circularly polarized luminescence liquid crystals mechanochromism mechanoluminescence structure-property relationship

SCI

English

Others

WOS:000863275100001

2-s2.0-85139102749

Scopus

1.Key Laboratory of New Lithium-Ion Battery and Mesoporous Material,College of Chemistry and Environmental Engineering,Shenzhen University,Shenzhen,1066 Xueyuan Avenue, Nanshan,518055,China
2.Department of Chemistry,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Avenue, Nanshan,518055,China
3.School of Science and Engineering,Shenzhen Institute of Aggregate Science and Technology,The Chinese University of HongKong,Shenzhen,518172,China

Zhang，Hongyan,Chang，Xiaoyong,Ma，Chaoyang,et al. Two Cholesterol-Containing Pyrene Derivatives: Subtle Spacer Difference, Diverse Stimuli-Responsive Luminescence, Chirality, and Self-Assembly Behaviors[J]. ACS Applied Materials & Interfaces,2022,14(38):43926-43936.

Zhang，Hongyan,Chang，Xiaoyong,Ma，Chaoyang,Huang，Guangxi,Li，Bing Shi,&Tang，Ben Zhong.(2022).Two Cholesterol-Containing Pyrene Derivatives: Subtle Spacer Difference, Diverse Stimuli-Responsive Luminescence, Chirality, and Self-Assembly Behaviors.ACS Applied Materials & Interfaces,14(38),43926-43936.

Zhang，Hongyan,et al."Two Cholesterol-Containing Pyrene Derivatives: Subtle Spacer Difference, Diverse Stimuli-Responsive Luminescence, Chirality, and Self-Assembly Behaviors".ACS Applied Materials & Interfaces 14.38(2022):43926-43936.