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This work explores the syntheses, structures, photophysical properties, and photostability of benzodipyrenes (BDPs). BDPs were synthesized through an InCl 3 -AgNTf 2 -catalyzed, four-fold alkyne benzannulation reaction. The structures of BDP 4 a and its corresponding endoperoxide product were unambiguously confirmed by X-ray crystallography. The BDPs reported here can also be recognized as peri- and cata-benzannulated pentacenes with a non-functionalized central ring. Unlike the previous reported pentacene-based polycyclic aromatic hydrocarbons, the absorbances of the BDPs were blueshifted by ca. 40 nm relative to pentacene, even after extension of π-conjugation. The newly synthesized BDP products exhibit relatively good stability with half-lives as high as 4612 min in THF., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

The design of a relatively simple and efficient method to extend the π-conjugation of readily available aromatics in one-dimension is of significant value. In this paper, pyrenes, peropyrenes, and teropyrenes were synthesized through a double or quadruple benzannulation reaction of alkynes promoted by Brønsted acid. This novel method does not involve cyclodehydrogenation (oxidative aryl-aryl coupling) to arrive at the newly incorporated large arene moieties. All of the target compounds were synthesized in moderate to good yields and were fully characterized with the structures unambiguously confirmed by X-ray crystallography. As expected, photophysical characterization clearly shows increasing red-shifts as a function of extended conjugation within the fused ring systems., (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

A new oxygen-sensitive optical probe based on the [Tb(3,5-dcba) 3 ]⋅1/2 H 2 O (3,5-dcba=3,5-dichlorobenzoate) complex, which is chemically attached to a phosphine-oxide-functionalized polydimethylsiloxane is presented. The hybrid material shows green emission and transparency in the visible range. The optically sensitive probe is photostable under excitation at 350 nm and shows the highest oxygen sensitivity, I 0 /I 100 equal to 8.9 at 1 atm, among probes based on homonuclear lanthanide compounds. Furthermore its reversibility is demonstrated after several cycles ranging from 100 % N 2 to 100 % O 2 with response time of 8.5 s (N 2 →O 2 ) and recovery time of 49.5 s (O 2 →N 2 )., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)