Two-Photon Absorption Properties of Alkynyl-Conjugated Pyrene Derivatives

Abstract

A series of pyrene derivatives having 4-(N,N-dimethylamino)phenylethynyl groups as the substituent (1-5) have been synthesized and their two-photon absorption properties were investigated. Comparison of two-photon cross section (delta(max)) with related compounds reveals that pyrene is as efficient a pi-center as anthracene in two-photon materials. Moreover, the two-photon cross section (delta(max)) increased with the number of substituents reaching at the maximum value of 1150 GM for the tetra-substituted derivative (5). Furthermore, the two-photon action cross section (Phi delta(max)) of 5 is comparable to that the most efficient two-photon materials. This result provides a useful guideline to the design of efficient two-photon materials bearing pyrene as a pi-center.

Donor-acceptor substituted phenylethynyltriphenylenes – excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission

“…The dihedral angle between the plane of the triphenylene ring and the plane of the phenyl ring is 96° for 1g . These observations are comparable with the geometry of the corresponding pyrene derivatives reported earlier [31–32]. The HOMO and LUMO surfaces are shown in Fig.…”

Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes

“…For example, the emission maxima of the pyrenyl-substituted pyrenes 6, 7a/7b, and 8, consecutively shifted to longer wavelengths at 432, 451 and 465 nm respectively ( Figure 4a), in a manner similar to their absorption maxima. These results were also observed in some carbazole-based dendrimers [46] and several phenylethynyl-substituted pyrene derivatives [47,48]. Similar findings were observed in the tetrakisfluorenyl-substituted pyrene 10 ( max = 456 nm, red-shifted ca.…”

Experimental and computational thermodynamics of pyrene and 1-pyrenecarboxaldehyde and their photophysical properties

“…Pyrene and its derivatives have been studied intensively as organic chromophores [5,6], sensors [7,8], light emitting materials in OLEDs [9][10][11][12], organic field effect transistors (OFETs) [12,13] and organic photovoltaic devices (OPVs) [12]. Synthetic pyrene-appended systems are used as sensors for ATP [14], heparin [15], nucleotides [16,17], transition metal ions [18] and as probes to study protein conformation, conformational changes, protein folding and unfolding, protein-protein, protein-lipid, and protein-membrane interactions [19].…”