97083-12-0

Upstream product

• 121976-02-1 9-phenyl-10-phenylethynyl-9,10-dihydro-anthracene-9,10-diol 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 536-74-3 phenylacetylene 
• 115198-11-3 9-bromo-10-(2-phenylethynyl)anthracene 
• 98-80-6 phenylboronic acid 
• 523-27-3 9,10-Dibromoanthracene 
• 359435-47-5 9-bromo-10-iodo-anthracene 
• 1564-64-3 9-Bromoanthracene 

Downstream Products

• 58813-48-2 9-phenyl-10-cis-styryl-anthracene 
• 103161-55-3 2-phenyl-1-(10-phenyl-[9]anthryl)-ethanone 
• 121499-83-0 phenyl-(10-phenyl-[9]anthryl)-ethanedione 
• 115001-34-8 2-phenyl-1-(10-phenyl-[9]anthryl)-ethanol 
• 103398-51-2 (1RS,2SR)-1,2-diacetoxy-1-phenyl-2-(10-phenyl-[9]anthryl)-ethane 
• 103162-60-3 (1RS,2SR)-1-phenyl-2-(10-phenyl-[9]anthryl)-ethane-1,2-diol 

Relevant academic research and scientific papers

Effects of terminal biphenyl ring geometry on the photophysical properties ofcloso-o-carboranyl-anthracene dyads

Four anthracene-based compounds bearing phenyl (AC) or biphenyl (oAC,mAC, andpAC) substituents at C10 and acloso-o-carboranyl unit at C9 were prepared and fully characterized to establish a design strategy for enhancing the solution- and solid-state emissive properties ofcloso-o-carboranyl luminophores at ambient temperature. In all solid-state molecular structures, the anthracene moieties were severely distorted because of intramolecular steric hindrance, which indicated that structural variation around theo-carborane cage was strongly inhibited. Compared to the othero-carboranyl compounds,oAC, possessing anortho-type biphenyl group, exhibited much higher emission intensity, quantum efficiency, and radiative decay constant in tetrahydrofuran solution and film state at 298 K. The electronic transitions calculated for first excited states showed that emission originated from intramolecular charge-transfer (ICT) transitions involvingo-carborane. The ground-state energy barriers were calculated based on the relative energies at dihedral angles centered at the bonding axis between anthracene and (bi)phenyl groups and implied that the rotational motion of the terminal (bi)phenyl rings was less restricted inoACthan in the other compounds. Furthermore, the orbital contributions calculated for electronic transitions in the first excited state indicated that structural variation around the terminal (bi)phenyl rings suppressed ICT transitions. The above findings reveal that the molecular rigidity of the moiety appended to aromatic rings ino-carboranyl-anthracene dyads strongly affects the efficiency of their ICT-based emission and suggest that this emission can be enhancedviathe attachment of rigid substituents too-carboranyl luminophores.

Bodipy-Phenylethynyl Anthracene Dyad: Spin-Orbit Charge Transfer Intersystem Crossing and Triplet Excited-State Equilibrium

Spin-orbit charge transfer-induced intersystem crossing (SOCT-ISC) is a promising method to design heavy atom-free triplet photosensitizers (PSs). Herein, a new organic triplet PS, BDP-An (Bodipy-phenylethynyl anthracene dyad) has been synthesized and studied. In polar solvents, charge transfer (CT) emission band was observed, and the singlet oxygen quantum yield (ΦΔ) is up to 95%. From femtosecond transient absorption (fs TA) spectra, SOCT-ISC mechanism was verified, the charge separation (CS) time takes1.6 ps, the lifetime of charge recombination (CR) is 3.8 ns, moreover the triplet state of phenylethynyl anthracene was also observed. In nanosecond transient absorption (ns TA) spectra, long-lived triplet states (τT =108 μs) were observed, which are delocalized on both parts of the dyad, i.e. there is a triplet excited-state equilibrium. This is the first report on the triplet excited-state equilibrium observed in an electron donor/acceptor dyad showing SOCT-ISC. With BDP-An as the triplet donor and perylene as the triplet acceptor, triplet-triplet annihilation upconversion (TTA UC) was performed, the upconversion quantum yield was up to 18.9%, and the lifetime of TTA-based delayed fluorescence was determined as 70.8 μs.

Phenyleneanthracene derivatives as triplet energy acceptor/emitter in red light excitable triplet-triplet-annihilation upconversion

A series of anthracene derivatives with 9,10-substituents were prepared as triplet acceptors/emitters for triplet-triplet-annihilation (TTA) upconversion. Different linkages of C[sbnd]C single bonds and C[tbnd]C triple bonds were used to tune the singlet and triplet state energy levels, which may enhance the TTA upconversion. The study of the photophysical properties of the compounds indicates that the C[sbnd]C linker does not alter the T1 state energy level substantially, whereas the C[tbnd]C linker significantly reduced the T1 state energy levels. With nanosecond transient absorption spectroscopy, the intermolecular triplet-triplet-energy-transfer (TTET) process was studied. The lack of the upconversion for some anthracene derivatives was attributed to the inappropriate T1 energy levels thus the lack of TTET. On the other hand, different upconversion quantum yields were observed for some acceptors, although the TTET processes are similar. This result is due to the different TTA. These studies will be useful for future development of the TTA upconversion and for study of the triplet state properties of organic chromophores.

Why triple bonds protect acenes from oxidation and decomposition

An experimental and computational study on the impact of functional groups on the oxidation stability of higher acenes is presented. We synthesized anthracenes, tetracenes, and pentacenes with various substituents at the periphery, identified their photooxygenation products, and measured the kinetics. Furthermore, the products obtained from thermolysis and the kinetics of the thermolysis are investigated. Density functional theory is applied in order to predict reaction energies, frontier molecular orbital interactions, and radical stabilization energies. The combined results allow us to describe the mechanisms of the oxidations and the subsequent thermolysis. We found that the alkynyl group not only enhances the oxidation stability of acenes but also protects the resulting endoperoxides from thermal decomposition. Additionally, such substituents increase the regioselectivity of the photooxygenation of tetracenes and pentacenes. For the first time, we oxidized alkynylpentacenes by using chemically generated singlet oxygen (1O2) without irradiation and identified a 6,13-endoperoxide as the sole regioisomer. The bimolecular rate constant of this oxidation amounts to only 1 × 10 5 s-1 M-1. This unexpectedly slow reaction is a result of a physical deactivation of 1O2. In contrast to unsubstituted or aryl-substituted acenes, photooxygenation of alkynyl-substituted acenes proceeds most likely by a concerted mechanism, while the thermolysis is well explained by the formation of radical intermediates. Our results should be important for the future design of oxidation stable acene-based semiconductors.