UV absorption and fluorescence properties of fused aromatic hydrocarbons having trimethylsilyl, trimethylgermyl, and trimethylstannyl groups

Abstract

Effects of trimethylsilyl, trimethylgermyl, and trimethylstannyl substituents attached to fused aromatic hydrocarbons such as pyrene, anthracene, phenanthrene, and naphthalene were studied in terms of UV absorption and fluorescence properties in aerated cyclohexane solutions. Absorption maxima of trimethylsilyl-, trimethylgermyl-, and trimethylstannyl-substituted aromatic hydrocarbons shifted to longer wavelengths than those of unsubstituted ones. Absorption maxima of mono-, bis-, tris-, and tetrakis(trimethylsilyl)pyrenes shifted to longer wavelength consecutively at intervals of 10 nm. Fluorescence intensities and fluorescence lifetimes of trimethylsilyl-substituted aromatic hydrocarbons were larger and longer than those of unsubstituted ones, and they decreased in the order of Me 3 SiAr [ Me 3 GeAr [ Me 3 SnAr. Fluorescence intensity of 1,3,6,8-tetrakis(trimethylsilyl)pyrene was largest among those of a series of mono-, bis-, tris-, and tetrakis(trimethylsilyl)pyrenes under aerated conditions.

Absorption and Fluorescence Spectroscopic Properties of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives

“…Close examination of these spectra shows that substituents on silicon of the silyl groups (SiMe 3 , SiMe 2 H, SiMe 2 n Bu, SiMe 2 t Bu, and SiMe 2 n Oct) have only a small effect on the absorption and fluorescence properties of the naphthalene chromophore/fluorophore. In contrast, silyl-substituents at C-9 of anthracene bring about dramatic changes in absorption and fluorescence properties [20,34]. A possible reason for this phenomenon is steric repulsion, which exists between the C-9 silyl groups and peri-hydrogens at C-1 and C-8 of the anthracene ring.…”

“…In addition, the enhancing effects of silyl groups on the fluorescence intensities of aromatic hydrocarbons, such as anthracenes, naphthacenes, pentacenes, triphenylenes, and pyrenes, has been probed and discussed in detail earlier [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29]. Our previous studies in this area have focused on the effects of silyl, silylethynyl, germyl, and stannyl groups on the absorption and fluorescence spectroscopic properties of pyrene [30][31][32][33][34]. In the photochemistry of silylnaphthalenes, the absorption and fluorescence properties as well as the photoreactions of disilanes [35][36][37][38][39] and oligosilanes [40][41][42] have been subjected to detailed investigation.…”

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

“…In investigations carried out recently, we designed and synthesized a variety of functional fluorescent materials that contain the pyrene fluorophore (52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63). In these studies, we observed that alkynylpyrenes are highly emissive and, as a result, they can be utilized as fluorescent probes for the detection of amino acids, proteins and DNA (53).…”

Fluorescence properties of 1-(silylethynyl)naphthalenes and 1,4-bis(silylethynyl)naphthalenes in solutions, thin films and solid states

“…Organic substances have some advantages in applications to photoactive materials because they possess unique luminescence properties that are governed by precise molecular designs [1][2][3][4][5][6]. Previously, we and others observed that linking silyl and silylethynyl groups to fused aromatic substances such as naphthalene [7][8][9], anthracene [7,10,11], pyrene [7,[12][13][14][15][16][17] and perylene [18] often increases fluorescence efficiency. However, the highly emissive character of these molecules is limited to highly dilute solutions because fluorescence intensities generally decrease as the concentrations of solutions increase.…”