1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

Abstract

We have synthesized 1,4,7,10-tetraisoalkyltetracenes from a 2,6-naphthodiyne precursor and 2,5-diisoalkylfurans as the starting materials (isoalkyl: isopropyl, isobutyl, and isopentyl). The tetracene molecules exhibited crystallochromy: The solid-state colors of the isopropyl, isobutyl, and isopentyl derivatives were yellow, red, and orange-yellow, respectively. In contrast, there were no marked differences in the optical properties of these compounds in solution. The isopropyl derivative exhibited the highest fluorescence quantum yield in

Arynes in the synthesis of polycyclic aromatic hydrocarbons

“…56 Similarly, Barrett and co-workers reported that the cycloaddition of 1,4-difluoro-2,5-dimethoxybenzene 5 as a 70 dienophile precursor with furan derivatives 6 afforded a series of functionalized anthracenes 11 and 12. In this example, 1,4difluoro-2,5-dimethoxybenzene 5 was used as iterative double benzyne as shown in Scheme 3.…”

“…As shown in 15 Scheme 4, the bis(aryne) precursor compound 13 was subjected to a Diels-Alder reaction with 2,5-dialkylfurans 14 followed by deoxygenation of the adduct 15 in the presence of hydrogen and Pd/C to afford 1,4,7,10-tetraalkyl tetracene 16. [68][69][70][71] In addition, unsubstituted pentacene can also be synthesized by using an 20 aryne as the starting material. Müllen's group reported the use of pentacene and nonacene precursors.…”

1,7-Diethyl-4,10-diisopropyltetracene

“…For the synthesis, see: Kitamura et al (2011). For structures of related alkylsubstituted tetracene derivatives, see: Kitamura, Abe et al (2010); Kitamura, Tsukuda et al (2010).…”

“…addition, we have recently found that alkyl-substituted tetracenes possess interesting chromophore properties. Depending on the length, shape, and the number of alkyl side chains, the solid-state color of the tetetracenes varies through yellow, orange and red (Kitamura, Abe et al, 2010;Kitamura, Tsukuda et al, 2010). The difference in color can be attributed to crystallochromy (Klebe, et al, 1989), i.e.…”

1,4,5,8-Tetraisopropylanthracene

“…For the preparation and solid-state fluorescence studies of 1,4,5,8-tetraalkylanthracenes, see: Kitamura et al (2007). For a related structure, see: Kitamura et al (2010). For related herringbone structures, see: Curtis et al (2004).…”