Organic Room‐Temperature Phosphorescence with Strong Circularly Polarized Luminescence Based on Paracyclophanes

Abstract

Pure organic materials with intrinsic room‐temperature phosphorescence typically rely on heavy atoms or heteroatoms. Two different strategies towards constructing organic room‐temperature phosphorescence (RTP) species based upon the through‐space charge transfer (TSCT) unit of [2.2]paracyclophane (PCP) were demonstrated. Materials with bromine atoms, PCP‐BrCz and PPCP‐BrCz, exhibit RTP lifetime of around 100 ms. Modulating the PCP core with non‐halogen‐containing electron‐withdrawing units, PCP‐TNTCz and PCP‐PyCNCz, successfully elongate the RTP lifetime to 313.59 and 528.00 ms, respectively, the afterglow of which is visible for several seconds under ambient conditions. The PCP‐TNTCz and PCP‐PyCNCz enantiomers display excellent circular polarized luminescence with dissymmetry factors as high as −1.2×10−2 in toluene solutions, and decent RTP lifetime of around 300 ms for PCP‐TNTCz enantiomers in crystalline state.

Stimuli‐Responsive Circularly Polarized Organic Ultralong Room Temperature Phosphorescence

“…The recent development of room temperature phosphorescence (RTP) of purely organic materials, especially organic ultralong RTP (OURTP) with lifetimes over 100 ms has significantly shaped the understanding of organic optoelectronics . However, it remains a daunting challenge to implant CPL in metal‐free RTP materials, let alone in OURTP molecules . Previous attempts only succeed in two multi‐component host‐guest and ionic cocrystal systems, showing circularly polarized OURTP (CP‐OURTP) with lifetimes of ≈0.67 and 0.86 s and dissymmetry factors ( g lum ) of ≈4.5×10 −4 and 2.0×10 −4 , respectively.…”

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

“…Different types of chiral scaffolds have been used to place the achiral chromophores in a chiral environment. Remarkable examples are binaphtyl-type skeletons (Hara et al, 2019;Takaishi et al, 2019), dibenzo [b,d]furane (Ito et al, 2017), cyclophanes (Morisaki et al, 2014;Liang et al, 2019;Wang et al, 2020), or [n]-helicenes (Dhbaibi et al, 2020). In this work, we considered as chiral scaffold enantiopure and commercially available (1R,2R)-(-)-1,2-diaminecyclohexane for its simplicity and its easy functionalization.…”

Optically Ambidextrous Reflection and Luminescence in Self-Organized Left-Handed Chiral Nematic Cellulose Nanocrystal Films

“…These observations are unprecedented as left-handed chiral nematic CNC films enable PBG-based RCP luminescence only due to the forbidden propagation of LCP luminescence. [54][55][56][57][58][59] CP luminescence spectra of CNC/PF-10BT-c-T and corresponding g lum values along with the transmission spectra showed systematic changes in the CP luminescence properties (Figure 4, Scheme 1). For example, a well-resolved RCP luminescence signal with |g lum | values up to 0.796 was observed for CNC/PF-10BT-4-4 prepared at low evaporation temperature and CNC suspension concentration (Figure 4a and 4b).…”