5737-94-0Relevant articles and documents
Soluble Twisted Diarenoperylenes: Synthesis, Characterization, and Device Performance
Liu, Xinyue,Chen, Meng,Xiao, Chengyi,Xue, Ning,Zhang, Lei
, p. 4512 - 4515 (2018)
Two stable TIPS-ethynyl functionalized polycyclic aromatic hydrocarbons (PAHs), dibenzo[a,j]perylene (TIPS-DBP), and dinaphtho[a,j]perylene (TIPS-DNP), which contain two rows of linear acenes joined by benzene rings, have been synthesized and characterized. It is found that the two twisted PAHs easily form one-dimensional charge-transport systems with short C-C contacts. The crystal of TIPS-DBP shows a hole mobility up to 0.17 cm2 V-1s-1, while the crystal of TIPS-DNP shows a hole mobility up to 0.74 cm2 V-1 s-1.
Photolysis of the Endoperoxide of Heterocoerdianthrone. A Concerted, Adiabatic Cycloreversion Originating from an Upper Excited Singlet State
Schmidt, R.,Drews, W.,Brauer, H.-D.
, p. 2791 - 2797 (1980)
In the present work we report the photolysis of the endoperoxide (PO) of heterocoerdianthrone (HCD = dibenzoperylene-8,16-dione).Two different photoreactions were observed: (1) an irreversible decomposition of PO, whose reaction products were not analyzed (this reaction occurs with a quantum yield of Qdec = 0.006 either from the S1(n,?*) state or, more probably, from the T1(n,?*) state); (2) a photoreversible cleavage of PO into HCD and O2 (this reaction originates from the S2(?,?*) state with a maximum quantum yield of Q1 = 0.26).Only the very rapid internal conversion from S2(?,?*) to S1(n,?*) competes with photoreaction.The products of photocleavage are HCD in its ground state and O2 in an electronically excited singlet state.These results confirm for the first time the predictions made by Kearns and Khan on the basis of state correlation diagrams concerning the concerted photocleavage of endoperoxides.
Aromatization of Benzannulated Perylene-3,9-diones: Unexpected Photophysical Properties and Reactivity
Rao, M. Rajeswara,Johnson, Shea,Perepichka, Dmitrii F.
, p. 3574 - 3577 (2016)
Highly unusual properties of acene-based quinones 1A and 1T are reported. They undergo an unexpected combination of Michael and carbonyl additions of aryllithium leading to new triarylated benzoperylenes 3A and 3T. Uncharacteristically for quinones, 1A and 1T display vibronically split absorption bands and small Stokes shifts. The absorption/emission spectra of the highly emissive 1A are almost indistinguishable from those of the aromatized 3A. Additional benzene rings cause a counterintuitive blue shift of the aromatic derivatives (2T/3T), but an expected red shift was observed for the quinone (1T). This behavior is fully supported by DFT calculations and rationalized by considering the longest conjugation path.
High Reactivity of Heterocoerdianthrones (HCDs) in Photoperoxidation and Thermal Stability of Their Endoperoxides. Use of HCD as a Photosensitizer under Sunlight
Motoyoshiya, Jiro,Masunaga, Takashi,Harumoto, Daisuke,Ishiguro, Shigeru,Narita, Susumu,Hayashi, Sadao
, p. 1166 - 1171 (2007/10/02)
The measured reactivity indices (β-values) of heterocoerdianthrones (HCDs) in self-sensitized photoperoxidation indicate a high reactivity toward singlet-oxygen.Such a high reactivity is not only due to an effective singlet-oxygen production due to the highly fluorescent character, but also due to a strained strucuture as predicted by a molecular calculation.On the other hand, the large thermal stability of their endoperoxides (POs), revealed by the large activation energy in thermal decomposition, is also explained by considering the strained structure of the parent HCDs.As a prospect of solar synthesis, one of the HCD derivatives was applied to a photosensitizer for singlet-oxygen oxidation.
