Abstract
Eight 9,10-disubstituted anthracenes have been synthesized, photochemically characterized and used for triplet–triplet annihilation photon upconversion.
Highlights
Anthracene and its derivatives have played an important role as organic chromophores since its discovery in 1832 by Jean B
Many dyes are based on the anthracene structure and applications for these blue emitting chromophores are plentiful in a variety of fields, from organic light emitting diodes (OLEDs)[3,4,5] and fluorescent probes[6,7,8] to organic scintillators[9] and more recently photon-upconversion through triplet–triplet annihilation.[10,11,12,13,14,15,16,17,18,19,20,21]
Absorption spectra and molar absorptivities of the five representative anthracene derivatives are presented in Fig. 4
Summary
Anthracene and its derivatives have played an important role as organic chromophores since its discovery in 1832 by Jean B. Substituting anthracene at the 9- and 10-positions can drastically alter the probability of these transitions, e.g. 9,10-dimethylanthracene has a fluorescence quantum yield of about 70%23 and has been successfully used in triplet–triplet annihilation systems. First a low energy photon is absorbed by a sensitizer in its ground state (1S) which readily undergoes intersystem crossing (ISC) to its first excited triplet state (3S*). To complement the experimental measurements DFT calculations of the position of singlet and triplet excited states were performed in order to determine the S–T energy level spacing. Both electron withdrawing and electron donating substituents have been chosen. The derivatives are compared to the well-known 9,10-diphenylanthracene (1) and 9,10-dimethylanthracene (2) chromophores
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