Azapyrene-based fluorophores: synthesis and photophysical properties

Abstract

Azapyrenes are the nitrogen isosteres of pyrene. Obviously, based on theoretical and experimental studies, the electron-acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of...

Synthesis and Properties of Diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines

“…[1,2] In the last decades, large π-conjugated polycyclic aromatic hydrocarbons (PAHs) and their heteroaromatic counterparts have received a lot of attention, due to their broad spectrum of applications. [3][4][5][6][7] In this context, nitrogen is the by far most often used element for the doping of PAHs. [3] Doping the aromatic structure with a pyridine-type nitrogen atom alters the molecular topology and allows for the modification of the key optical and electrochemical properties, such as photoluminescence, redox behavior, optical absorption, stabilized HOMO-LUMO energy levels, narrow electronic band gaps, and increased electron-acceptor ability.…”

“…[3] Doping the aromatic structure with a pyridine-type nitrogen atom alters the molecular topology and allows for the modification of the key optical and electrochemical properties, such as photoluminescence, redox behavior, optical absorption, stabilized HOMO-LUMO energy levels, narrow electronic band gaps, and increased electron-acceptor ability. [4,[8][9][10][11][12] Thus, more recent applications of N-doped PAHs include fluorescence sensors, [3] fluorophores, [7] two-photon absorbers, [13] ligands for transition metal complexes, [3,6] and organic materials in material sciences, especially in the field of molecular electronics. [3,4] This includes applications in organic light emitting diodes (OLEDs), [14] organic photovoltaic cells (OPVs), [15] and organic field-effect transistors (OFETs).…”

“…[12,16] In addition, they are promising candidates for the development of self-organizing compounds. [5,7,17] 2-Azapyrene (D) represents an important N-doped PAH which possesses several technical applications (Scheme 1). [18] However, π-extended 2-azapyrenes, containing annulated aromatic rings in the K-region, have only scarcely been reported.…”

2,7-Diazapyrenes: a brief review on synthetic strategies and application opportunities

“…Changing the molecular architecture of the pyrene core by doping the carbon framework with heteroatoms, for instance, pyridine-type nitrogen, proved to be an effective strategy for tuning the electrochemical and optical properties of the resulted hetero-PAHs. 31 The 2,7-diazapyrene derivatives, as nitrogen-doped analogues of pyrene, should have possess highly efficient optoelectronic properties. However, studies of the parent 2,7-diazapyrene 1 remain limited due to the lack of effective pathways for the synthesis of 2,7-diazapyrene derivatives.…”

A terpyridine-appended hexaarylbenzene fluorophore: synthesis, photophysical properties and application for the colorimetric detection of Fe2+ in aqueous solution

“…The development of organic fluorophores that contain both electron-donor (D) and electron-acceptor (A) units has attracted increasing attention due to their widespread applications. [1][2][3][4][5][6][7][8][9][10] A notable feature of such push-pull molecules is the intramolecular charge transfer (ICT) that occurs from the donor to the acceptor, which is vital in determining their optical and electronic properties. In this context, most push-pull fluorophores are known to show a lower fluorescence intensity/efficiency and a longer emission wavelength in a more polar environment (tentatively denoted as downhill-type emission).…”