Two novel chiral AIEgens as coordination precursors: synthesis, structures and photophysical study.

Spectrochim Acta A Mol Biomol Spectrosc

School of Chemistry & Environmental Engineering, Yancheng Teachers University, Yancheng 224007, PR China; New Energy Photovoltaic Industry Research Center, Qinghai University, Xining, Qinghai 810016, PR China; Key Laboratory of Functional Molecule Design and Interface Process, Anhui Jianzhu University, Hefei 230601, PR China. Electronic address:

Published: April 2024

AI Article Synopsis

  • Two chiral molecules, OCCA and TPCA, were synthesized and characterized using aldehyde amine condensation, H NMR, and single crystal X-ray diffraction.
  • These molecules exhibit unique photoluminescence properties, changing colors when they aggregate—OCCA emits purple-blue light (388 nm) while TPCA emits cyan light (488 nm).
  • The observed aggregation-induced emission (AIE) effects are attributed to mechanisms involving twisted intermolecular charge transfer (TICT) and restriction of intramolecular motion (RIM), along with detailed discussions on their UV-vis, IR, and Raman spectra.

Article Abstract

Two novel chiral molecules, (4S)-5,5-dimethyl-2-(4-oxo-4H-chromen-3-yl)thiazolidine-4-carboxylic acid (OCCA) and (4S)-5,5-dimethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)thiazolidine-4-carboxylic acid (TPCA), were successfully synthesized by aldehyde amine condensation reaction, and their structures were characterized by H NMR and single crystal X-ray diffraction. The intensities of photoluminescence changed with the aggregation, exhibiting that OCCA and TPCA are aggregation-induced emission luminogens (AIEgens). After complete aggregation, OCCA emitted the purple-blue light at the peak of 388 nm and TPCA emitted the cyan light at the peak of 488 nm. The aggregation-induced emission (AIE) effects for OCCA and TPCA resulted from local state to twisted intermolecular charge transfer (TICT) and restriction of intramolecular motion (RIM), respectively. Other spectra including UV-vis, IR, and Raman spectra were also discussed in detail.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.saa.2024.123960DOI Listing

Publication Analysis

Top Keywords

novel chiral
8
occa tpca
8
aggregation-induced emission
8
light peak
8
chiral aiegens
4
aiegens coordination
4
coordination precursors
4
precursors synthesis
4
synthesis structures
4
structures photophysical
4

Similar Publications

The development of chirality descriptors for quantitative chirality structure-activity relationship (QCSAR) modeling has always attracted attention, owing to the importance of chiral molecules in pharmaceutical, agriculture, food, and fragrance industries, and environmental toxicology. The utility of a multidimensional space of novel relative chirality indices (RCIs) in the QCSAR modeling of twenty CCR2 antagonists is reported upon in this paper. The numerical characterization of chirality by the RCI approach gives a large pool of chirality descriptors with different degrees of mutual correlation (the correlation coefficient among the computed descriptors varied from 0.

View Article and Find Full Text PDF

Glycans, unlike uniformly charged DNA and compositionally diverse peptides, are typically uncharged and exhibit rich stereoisomeric diversity in the glycosidic bonds between two monosaccharide units. This heterogeneity of charge and the structural complexity present significant challenges for accurate analysis. Herein, we developed a novel single-molecule oligosaccharide sensor, OmpF nanopore.

View Article and Find Full Text PDF

Noncovalent forces have a significant impact on photophysical properties, and the flexible employment of weak forces facilitates the design of novel luminescent materials with a variety of applications. The arene-perfluoroarene (AP) force, as one type of π-hole/π interaction, shows unique directionality, involving an electron-deficient π-hole interacting with a π-electron-rich region, facilitating precise orientation and stabilization in supramolecular structures. Here we present an amination engineering protocol to build a perfluoroarene library based on an octafluoronaphthalene skeleton with various steric and electronic properties.

View Article and Find Full Text PDF

Chirality plays a crucial role in the pharmacological activity of triazoles, a key scaffold in antifungal agents and various therapeutic applications. This study focuses on optimizing the enantiomeric resolution of chiral triazoles using supercritical fluid chromatography (SFC) and 10 different columns, either immobilized or coated, chlorinated or nonchlorinated, cellulose or amylose-based chiral stationary phases (CSPs). Four novel triazoles and two marketed ones (tebuconazole and hexaconazole) were separated to determine optimal resolution conditions.

View Article and Find Full Text PDF

Catalytic Asymmetric Dehydrogenative Si-H/X-H Coupling toward Si-Stereogenic Silanes.

Acc Chem Res

January 2025

Shenzhen Grubbs Institute and Department of Chemistry, Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China.

ConspectusChiral organosilicon compounds bearing a Si-stereogenic center have attracted increasing attention in various scientific communities and appear to be a topic of high current relevance in modern organic chemistry, given their versatile utility as chiral building blocks, chiral reagents, chiral auxiliaries, and chiral catalysts. Historically, access to these non-natural Si-stereogenic silanes mainly relies on resolution, whereas their asymmetric synthetic methods dramatically lagged compared to their carbon counterparts. Over the past two decades, transition-metal-catalyzed desymmetrization of prochiral organosilanes has emerged as an effective tool for the synthesis of enantioenriched Si-stereogenic silanes.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!