13929-87-8

Upstream product

• 39115-40-7 Phthaloyltriptycen 
• 106750-94-1 C₂₈H₂₀ 
• 108947-36-0 5,14-<1',2'-benzeno>5,5a,6,14-tetrahydropentacene 
• 120-12-7 anthracene 
• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 36439-82-4 9,10-dihydro-11,12-dimethylene-9,10-ethanoanthracene 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 106-37-6 1.4-dibromobenzene 
• 106750-88-3 6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene 
• 106750-31-6 C₂₄H₁₆O 
• 1276025-67-2 C₂₈H₁₈O 
• 1276026-07-3 5,6-(9,10-dihydroanthracen-9,10-yl)isobenzofuran 
• 4831-47-4 2-amino-3-anthracenecarboxylic acid 
• 106750-90-7 C₂₄H₁₆Br₂O 

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.

New Iptycenes Using 2,3-Naphthotriptycene as a Synthon

A new synthesis of the triptycene 1 (5,14-benzeno-5,14-dihydropentacene) is described.Cycloaddition of endoxide 8 to diene 6 gave exo adduct 9, which was successively dehydrated and dehydrogenated to give 1 in three steps and 47percent overall yield.Cycloadducts 11-13 were obtained from 1 and tetracyanoethylene, dimethyl acetylenedicarboxylate, or maleic anhydride, respectively.Irradiation of 1 through Pyrex gave photodimer 26.Pentiptycenes 16 and 18 were obtained in two steps using 1 as a synthon.Cycloaddition of 1,4-dichloro-2-butene to 1, followed by dehydrohalogenation, gave diene 21, which was then used as a synthon for functionalized pentiptycenes 22 and 25.Finally, the new route to 1 was extended to the first synthesis of its naphthacene analogue 30.

Incorporation of Internal Free Volume: Synthesis and Characterization of Iptycene-Elaborated Poly (butadiene)s

The synthesis and characterization of a series of high molecular weight iptycene-containing polymers were presented. Several high molecular weight iptycene-containing polymers were synthesized through a thermally induced radical polymerization of butadien

A general and simple route to the synthesis of triptycenes

A general and simple route to the synthesis of the triptycene derivatives 5,12-dihydro-5,12[1',2']-benzenonaphthacene (1), 5,14-dihydro-5,14[1',2']-benzenopentacene (2) and 5,16-dihydro-5,16[1',2']-benzenohexacene (3) is described. It involves the cycloaddition of appropriate quinone to anthracene and subsequent treatment of the resulting adduct with lithium aluminium hydride, followed by p-toluenesulfonyl chloride in pyridine.

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.

IPTYCENES EXTENDED TRIPTYCENES

Triptycene is the first member of a large scale of compounds for which we have coined the general term "iptycenes".The prefix (tri, pent, etc.) indicates the number of separated arene planes.By fusing from one to six 9,10-anthradiyl moieties on the triptycene framework, one can derive a first generation of iptycenes (Table 1).Of these, only 3, 4, 8 and a substituted 2 are known; the remainder provide a synthetic challenge.Potentially interesting practical and theorethical properties of iptycenes and particular structural features of several (i.e. 15, 16 and 24) arebriefly discussed, as are certain extensions beyond the compounds in Table 1.Methods for preparing useful synthons 35-41 are described.Three new, much improved syntheses of triptycene 29, itself a useful iptycene synthon, are presented.In addition, improved syntheses of pentiptycenes 3 and 33 are described, as well as the first syntheses of pentiptycenes 32, 34 and 52 and heptiptycene 54.The way is paved for future development of this mini-domain of unnatural products.