Multiply Twisted Chiral Macrocycles Clamped by Tethered Binaphthyls Exhibiting High Circularly Polarized Luminescence Brightness

Abstract[2.2]Paracyclophanes ([2.2]PCs) with substituents at specific positions possesses planar chirality and stands as a promising building unit for the development of chiroptical materials associated with polarized light. However, one of the easily accessible starting materials, bromo‐substituted [2.2]PC, shows low reactivity, and effective methods for π‐extension of planar chiral [2.2]PC are limited. Herein, an effective π‐extension method has established for chiral [2.2]PC with four substitutions from 4,7,12,15‐tetrabromo[2.2]PC. This has led to tetrakis(trimethylsilylphenyl)‐[2.2]PC that serves as a versatile building resource for radial‐type chiral π‐conjugated compounds with a [2.2]PC core. In this study, synthesizing compounds are further succeeded with the introduction of carbazole (Cbz4‐[2.2]PC and tBuCbz4‐[2.2]PC) and investigated their chiroptical properties and chiral induction ability in achiral π‐conjugated polymers. A thin film of [Poly[9,9‐dioctylfluorenyl‐2,7‐diyl)‐alt‐(benzo[2,1,3]thiadiazol‐4,7‐diyl)]] (F8BT) with 3wt% Cbz4‐[2.2]PC prepared by spin‐coating exhibits circularly polarized luminescence (CPL) properties with a high dissymmetry factor (|glum| = 0.01), which is much higher than that of Cbz4‐[2.2]PC in CH2Cl2 solution. By contrast, the doped film of F8BT with 3wt% tBuCbz4‐[2.2]PC exhibited only weak CPL properties. In addition, these chiral compounds show facile redox properties owing to the presence of carbazole units. Furthermore, Cbz4‐[2.2]PC undergoes electropolymerization to produce an insoluble thin film on the electrode.

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Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

Xue,

Shi,

Chen

2024

Advanced Optical Materials

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Molecular chirality plays a pivotal role across the disciplines of chemical and physical sciences, as well as holding significant implications in the realms of medicine and technology. Chiral macrocycles have attracted recent interests in synthetic chemistry, material science, and supramolecular chemistry. Due to the cyclic arrangements of stereogenic elements or special orientations confined in the rigid structures, π‐conjugated chiral macrocycles are expected to be highly luminescent, and configurationally stable, and thus serve to develop high‐performance chiroptical materials. Given the rapid progress achieved in this new area in recent years, it is significant to highlight new concepts and breakthroughs. This minireview will offer the overview of a wide range of π‐conjugated chiral macrocycles from traditional molecules which include the axially, helically, and planar chiral skeletons to the new chiral nanobelts with a focus on the structure‐function relationship between chiral molecules and the unique chiroptical properties.

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Multiply Twisted Chiral Macrocycles Clamped by Tethered Binaphthyls Exhibiting High Circularly Polarized Luminescence Brightness

Cited by 25 publications

References 54 publications

Circularly Polarized Luminescence in Stereogenic π‐Conjugated Macrocycles

Circularly Polarized Luminescence in Stereogenic π‐Conjugated Macrocycles

Synthesis and Chiroptical Properties of Radially Extended Carbazole with Chiral [2.2]Paracyclophane Core

Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

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