39115-40-7

Upstream product

• 120-12-7 anthracene 
• 4831-47-4 2-amino-3-anthracenecarboxylic acid 
• 106750-31-6 C₂₄H₁₆O 
• 1276025-67-2 C₂₈H₁₈O 
• 1276026-07-3 5,6-(9,10-dihydroanthracen-9,10-yl)isobenzofuran 
• 114260-65-0 C₂₈H₁₈O₃ 

Downstream Products

• 13929-87-8 5,14-dihydro-5,14<1',2'>-benzenopentacene 

Relevant academic research and scientific papers

Anthracene capped isobenzofuran: A synthon for the preparations of iptycenes and iptycene quinones

Anthracene capped isobenzofuran 5 (5,6-(9,10-dihydroanthracen-9,10-yl) isobenzofuran) was synthesized for the first time. It is a highly reactive and versatile synthon for the synthesis of iptycene derivatives via Diels-Alder reactions. Cycloadducts 10 could be readily deoxygenated to iptycenes 11. Two new reactions of PhI(OAc)2/TfOH have been explored. Endoxides 10 were directly oxidized to iptycene quinones 12, and isobenzofuran 5 was conveniently converted to triptycene dialdehyde 16. H-shaped centrally extended pentiptycene quinones 13 and 14 were also synthesized.

ULTRAFAST PHOTOINDUCED ELECTRON TRANSFER IN RIGID DONOR-SPACER-ACCEPTOR MOLECULES: MODIFICATION OF SPACER ENERGETICS AS A PROBE FOR SUPEREXCHANGE

Four fixed-distance porphyrin-quinone molecules, 1-syn, 1-anti, 2-syn, and 2-anti, were synthesized.These molecules possess a zinc 5-phenyl-10,15,20-tripentylporphyrin electron donor attached to a naphthoquinone via a rigid pentiptycene spacer.The central benzene ring of the spacer is unsubstituted in 1 and possesses p-dimethoxy substituents in 2.The naphthoquinone is oriented either syn or anti to the porphyrin across the spacer.These molecules provide information concerning the orientation dependence of electron transfer between the porphyrin and the quinone, and the dependence of this transfer on low-lying ionic states of the spacer.The rate constants for the oxidation of the porphyrin lowest excited state by the naphthoquinone are 1-syn: 8.2 x 10E9 s-1; 1-anti: 1.7 x 10E10 s-1; 2-syn: 8.5 x 10E9 s1-; 2-anti: 1.9 x 10E10 s-1.The corresponding rate constants for the porphyrin cation - naphthoquinone anion recombination reaction are 1-syn: 1.4 x 10E10 s-1; 1-anti: 2.5 x 10E10 s-1; 2-syn: 5.0 x 10E10 s-1; 2-anti: 8.2 x 10E10 s-1.The rate constant for the syn isomers are uniformly a factor of about 2 slower than those of the anti isomers.The charge separation reaction rates for 1 and 2 are similar, while the ion pair recombination reactions are about 3-4 x faster in 2 than in 1.The conformational effect is attributed to better overlap of the spacer wave functions in the anti vs the syn conformation, while the increase in recombination rate for 2 over 1 is attributed to a superexchange interaction involving an electronic configuration of the spacer in which the dimethoxybenzene cation contributes.