Host-guest complex solid state molecular motion is a critical but underexplored phenomenon. In principle, it can be used to control molecular machines that function in the solid state. Here we describe a solid state system that operates on the basis of complexation between an all-hydrocarbon macrocycle, D_4d-CDMB-8, and perylene. Molecular motion in this solid state machine is induced by exposure to organic solvents or grinding and gives rise to different co-crystalline, mixed crystalline, or amorphous forms. Distinct time-dependent emissive responses are seen for different organic solvents as their respective vapours or when the solid forms are subject to grinding. This temporal feature allows the present D_4d-CDMB-8⊃perylene-based system to be used as a time-dependent, colour-based 4th dimension response element in pattern-based information codes. This work highlights how dynamic control over solid-state host-guest molecular motion may be used to induce a tuneable temporal response and provide materials with information storage capability.

Yu Dong Yang;Xiaofan Ji;Zhi Hao Lu;Jian Yang;Chao Gao;Haoke Zhang;本忠 唐;Jonathan L. Sessler;Han Yuan Gong

Nature Communications

2020-12-1

Three amphiphilic block copolymers are employed to form polymeric micelles and function as nanocarriers to disperse hydrophobic aggregation-induced emission (AIE) dyes, 1,1,2,3,4,5-hexaphenylsiloIe (HPS) and/or bis(4-(N-(1-naphthyl) phenylamino)-phenyl)fumaronitrile (NPAFN), into aqueous solution for biological studies. Compared to their virtually nonemissive properties in organic solutions, the fluorescence intensity of these AIE dyes has increased significantly due to the spatial confinement that restricts intramolecular rotation of these dyes and their better compatibility in the hydrophobic core of polymeric micelles. The effect of the chemical structure of micelle cores on the photophysical properties of AIE dyes are investigated, and the fluorescence resonance energy transfer (FRET) from the green-emitting donor (HPS) to the red-emitting acceptor (NPAFN) is explored by co-encapsulating this FRET pair in the same micelle core. The highest fluorescence quantum yield (∼62%) could be achieved by encapsulating HPS aggregates in the micelles. Efficient energy transfer (>99%) and high amplification of emission (as high as 8 times) from the NPAFN acceptor could also be achieved by spatially confining the HPS/NPAFN FRET pair in the hydrophobic core of polymeric micelles. These micelles could be successfully internalized into the RAW 264.7 cells to demonstrate high-quality fluorescent images and cell viability due to improved quantum yield and reduced cytotoxicity.

Wen Chung Wu;Ching Yi Chen;Yanqing Tian;Sei Hum Jang;Yuning Hong;Yang Liu;Rongrong Hu;本忠 唐;Yi Ting Lee;Chin Ti Chen;Wen Chang Chen;Alex K.Y. Jen

Advanced Functional Materials

2010-5-10

Interaction of Ru(=CHPh)(PCy₃)₂Cl₂ (Cy = cyclohexyl) with K[N(PPh₂S)₂] affords air-stable Ru(=CHPh)[N(PPh₂S)₂]₂, 1, which has been characterized by X-ray diffraction. The Ru-Cα and average Ru-S distance for 1 are 1.88(2) and 2.377 Å, respectively. Reaction of 1 with CO gives sis-Ru(CO)₂[N(PPh₂S)₂]₂. Complex 1 undergoes metathesis with ethyl vinyl ether to give the methoxycarbene complex Ru(=CHOEt)[N(PPh₂S)₂]₂, 3. Treatment of Ru(=CHPh)-(PCy₃)₂Cl₂ with K[N(PPh₂Se)₂] affords Ru(=CHPh)[PPh₂NP(Se)Ph₂]₂, 4, which has been characterized by X-ray crystallography. The Ru-C, average Ru-P, and average Ru-Se distances are 1.873(8), 2.383, and 2.450 Å, respectively. Reactions of Ru(=CHPh)(PCy₃)₂Cl₂ with K[P(OR)₂S₂] afford cis-Ru(=CHPh)(PCy₃)[P(OR)₂S₂]₂ (R = Et (6) and i-Pr (7)). Reaction of Ru(=CHPh)(PCy₃)₂Cl₂ with 1,4,7-trithiacyclononane ([9]aneS₃) gives [([9]aneS₃)Ru-(=CHPh)(PCy₃)Cl]Cl, 8. Treatment of Ru(=C=CHPh)(PCy₃)₂Cl₂ with K[N(PPh₂S)₂] or [9]aneS₃ affords cis-Ru(=C=CHPh)(PCy₃)[N(PPh₂S)₂]₂ (9) or ([9]aneS₃)Ru(PCy₃)Cl₂ (10), respectively. The Ru-C, Ru-P, and average Ru-S distances in 9 are 1.80(1), 2.420(3), and 2.479 Å, respectively. Complexes 1 and 8 are active catalysts for ring-opening metathesis polymerization of norbornene.

Wa Hung Leung;Kwok Kin Lau;千峰 张;Wing Tak Wong;本忠 唐

Organometallics

2000-5-29

An oligo (phenylene vinylene) with central biphenyl bridge and peripheral carbazole founctionalities was synthesized. The structure and purity were characterized by using ¹H NMR, MS and elementary analysis techniques. Thermal analysis data indicated that the obtained compound possessed both high chemical and morphological stability. The glass transition temperature was 142.05°C ; the mass-loss temperature started at 306°C,. The observed absorption features and X-ray diffraction patterns suggested an amorphous state of the spin-coating films, and the annealing treatment at 80°C for 4 h did not change the amorphous property. The results above showed that the molecular design of introducing a central biphenyl bridge and bonding peripheral bulky carbazole functionalities can not only effectively decrease the aggregation of chromophores but also keep the stability of biphenyl bridged DSB derivatives.

Xue Liang Song;Jia Ke Jin;Hao Yu Dong;本忠 唐;Jing Zhi Sun

Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities

2006-11

The hybridization of functional polyacetylenes with lead bromide perovskite was investigated. It was observed that the perovskite induces the nonmesogenic polyactylene chains to align like liquid crystals within the inorganic layers. It was shown that photoenergy is efficiently transferred from the perovskite framework to the polyacetylene chains, and the chain interactions are suppressed by the segregation of the polymer chains in separate perovskite layers. It was found that the energy transfer and chain separation both help enhance the light emission efficiency of the hybrids.

Jianli Hua;Zhen Li;Jacky W.Y. Lam;Haipeng Xu;Jingzhi Sun;Yuping Dong;Yongqiang Dong;Anjun Qin;Wangzhang Yuan;Hongzheng Chen;Mang Wang;本忠 唐

Macromolecules

2005-10-4

The reported organic light-emitting diodes (OLEDs) based on hybridized local and charge-transfer (HLCT) state emitters mostly exhibit low photoluminescence quantum yields (PLQYs) in aggregates, failing to achieve optimal device efficiency although they exhibit good exciton utilization efficiencies (EUEs). In this work, by introducing an aggregation-induced emission (AIE) moiety (tetraphenylethene, TPE) and a cyano group (CN) to the HLCT-typed core, phenanthroimidazole (PI), six luminescent compounds with different conjugation patterns at the C2 and N1 substituent positions were obtained, and their excited states were regulated effectively. Based on systematic photophysical analysis, the impacts of molecular conjugation patterns on the regulation of the locally excited (LE) and charge-transfer (CT) components are disclosed, and their AIE characteristics that ensure the high PLQYs of these compounds in aggregates were observed. Exciton conversion channels from triplets to singlets via the tuning of excited states were proposed based on theoretical calculations. The non-doped OLED based on ppCTPI compounds exhibited excellent performance with a maximum luminance, current efficiency, and external quantum efficiency of up to 31070 cd m^-2, 18.46 cd A^-1, and 7.16%, respectively, and a very small efficiency roll-off of 4.0% at 1000 cd m^-2 luminance. The successful design of these HLCT-based AIEgens not only provides more optimization choices for OLED emitters, but also demonstrates that the strategy of reasonably superposing the AIE unit onto HLCT emitters is feasible in materials design.

Han Zhang;Jiajie Zeng;Wenwen Luo;Haozhong Wu;Cheng Zeng;Kexin Zhang;Weiqiang Feng;Zhiming Wang;Zujin Zhao;本忠 唐

Journal of Materials Chemistry C

2019

Application of a hydrostatic pressure in the range of 1-650 atm boosted photoluminescence and electroluminescence of hexaphenylsilole by ∼10 and ∼73%, respectively, due to the suppression of intramolecular rotations and/or the increase in carrier injection, offering a helpful mechanistic insight into the intriguing phenomenon of aggregation-induced emission.

星河 范;Jianliang Sun;Fuzhi Wang;Zengze Chu;Ping Wang;Yongqiang Dong;Rongrong Hu;本忠 唐;德春 邹

Chemical Communications

2008

Tetraphenylethene-containing diyne (1), named 1,2-bis(4-ethynylphenyl)-1,2- diphenylethene, was synthesized and polymerized by TaBr₅ catalyst, affording the hyperbranched polymer hb-P1 with a high molecular weight (M _w up to 157800) in a nearly quantitative yield. The cyclotrimerization of 1-(4-ethynylphenyl)-1,2,2-triphenylethene was also carried out to give 1,3,5- and 1,2,4-tris[4-(1,2,2-triphenylvinyl)phenyl]benzene (1,3,5-2 and 1,2,4-2) that served as model compounds for structural characterization and properties investigation. The structures of hb-P1 and 2 are characterized by MS, IR, and NMR spectroscopies with satisfactory results. All the molecules and polymer are completely soluble in common organic solvents such as chloroform, toluene and THF. They show high thermal stability with degradation temperatures up to 443 and 446°C, respectively, in nitrogen and air. Whereas their solutions are almost non-emissive or weakly fluorescent, their aggregates in poor solvents and solid powders emit intensely with fluorescence quantum yields up to 81%, demonstrating a novel phenomenon of aggregation-induced or enhanced emission. The unreacted triple bonds on the periphery of hb-P1 allow its thin film to cross-link under UV irradiation, generating well-resolved photopatterns. The hyperbranched polymer can limit harsh laser pulses. Its emission can be quenched efficiently by picric acid in solution and aggregated states with large quenching constants, suggesting that it is a promising fluorescent chemosensor for explosives detection.

Rongrong Hu;Jacky W.Y. Lam;Jianzhao Liu;Herman H.Y. Sung;Ian D. Williams;Zhounan Yue;Kam Sing Wong;Matthew M.F. Yuen;本忠 唐

Polymer Chemistry

2012-6

Fully understanding the complicated interplays among various chemical species and organelles is greatly important to unravel the mystery of life. However, fluorescent probes capable of visualizing multiple targets discriminatively are severely deficient, which extremely limit the investigation on intracellular interplays among various species. Towards this end and in consideration of the unique advantages of aggregation-induced emission luminogens (AIEgens), here we rationally designed and presented a single AIEgen, named TVQE, bearing lipophilic, cationic and hydrolyzable moieties, and this AIEgen was capable of illuminating mitochondria and lipid droplets with red and blue emission, respectively. In addition, TVQE was successfully used for evaluating cell viability due to its distinct two-color emission changes tuned by esterase-mediated hydrolysis. Of particular importance is that TVQE can selectively differentiate live, early apoptotic, late apoptotic, and dead cells by confocal microscopy and quantify cell viability statistically by flow cytometry.

Ruoyao Zhang;Guangle Niu;Zhiyang Liu;Joe H.C. Chau;Huifang Su;Michelle M.S. Lee;Yuan Gu;Ryan T.K. Kwok;Jacky W.Y. Lam;本忠 唐

Biomaterials

2020-6

Research on aggregation-induced emission (AIE) has become increasingly popular recently and various AIE luminogens (AIEgens) have been developed based on tetraphenylethene, hexaphenylsilole, distyrylanthracene, tetraphenylpyrazine, etc. However, facile tuning of the AIEgen emissions in a wide range remains challenging. Herein, a novel series of AIEgens is reported, based on imidazole-cored molecular rotors, with facile synthesis and emission colors covering the whole visible spectrum. Moreover, these imidazole derivatives exhibit biological functions unique among the AIEgens, including mitochondria-specific imaging and antifungal activity. Benefiting from the easy preparation and the tunable emission, the imidazole derivatives are expected to not only diversify the family of AIEgens but also enrich their biological applications.

Zhegang Song;Weijie Zhang;Meijuan Jiang;Herman H.Y. Sung;Ryan T.K. Kwok;Han Nie;Ian D. Williams;Bin Liu;本忠 唐

Advanced Functional Materials

2016-2-9