Substituent Effects on the Absorption and Fluorescence Properties of Anthracene

The 1,3a,6a-triazapentalene (TAP) is an aromatic heterocyclic fluorescent dye with interesting features such as its small size, large Stokes shift, solvatochromism, and emission wavelengths that are spread across the visible spectrum. TAPs have been synthesized via different synthetic strategies involving click−cyclization−aromatization domino reactions, gold-catalyzed cyclization of propargyl triazoles or triazolization of acetophenones. As a result, TAPs with diverse substitution patterns were obtained, showing varying fluorescence properties. Based on these properties, several TAPs have been selected and studied as fluorescent imaging probes in living cells and as sensors. This mini review provides an overview of the research on the bicyclic TAPs and does not comment on the literature about benzo or otherwise fused systems. The synthetic methodologies for the preparation of TAPs, the substituent effects on the fluorescence properties, and the behavior of the TAP core as an element of biological imaging probes and sensors are discussed.

Download Full-text

Fluorescence Properties of Diphenylthiazolo[4,5-b]pyrazines Tuned by Donor-Acceptor Substituent Effects

Photochemistry and Photobiology ◽

10.1111/php.12440 ◽

2015 ◽

Vol 91 (4) ◽

pp. 807-813 ◽

Cited By ~ 6

Author(s):

Tatsuki Nakagawa ◽

Minoru Yamaji ◽

Shojiro Maki ◽

Haruki Niwa ◽

Takashi Hirano

Keyword(s):

Substituent Effects ◽

Fluorescence Properties ◽

Acceptor Substituent ◽

Donor Acceptor

Download Full-text

Water-Soluble Fluorescent Boronic Acid Compounds for Saccharide Sensing: Substituent Effects on Their Fluorescence Properties

Chemistry - A European Journal ◽

10.1002/chem.200500982 ◽

2006 ◽

Vol 12 (5) ◽

pp. 1377-1384 ◽

Cited By ~ 42

Author(s):

Yanling Zhang ◽

Xingming Gao ◽

Kenneth Hardcastle ◽

Binghe Wang

Keyword(s):

Boronic Acid ◽

Substituent Effects ◽

Water Soluble ◽

Fluorescence Properties

Download Full-text

Substituent Effects on the Fluorescence Properties ofortho-Carboranes: Unusual Emission Behaviour inC-(2′-Pyridyl)-ortho-carboranes

European Journal of Inorganic Chemistry ◽

10.1002/ejic.201501284 ◽

2016 ◽

Vol 2016 (3) ◽

pp. 403-412 ◽

Cited By ~ 35

Author(s):

Lena Böhling ◽

Andreas Brockhinke ◽

Jan Kahlert ◽

Lothar Weber ◽

Rachel A. Harder ◽

...

Keyword(s):

Substituent Effects ◽

Fluorescence Properties

Download Full-text

Substituent effects on fluorescence properties of thiazolo[4,5-b]pyrazine derivatives

Photochemical & Photobiological Sciences ◽

10.1039/c4pp00298a ◽

2014 ◽

Vol 13 (12) ◽

pp. 1765-1772 ◽

Cited By ~ 6

Author(s):

Tatsuki Nakagawa ◽

Minoru Yamaji ◽

Shojiro Maki ◽

Haruki Niwa ◽

Takashi Hirano

Keyword(s):

Substituent Effects ◽

Phenyl Group ◽

Fluorescence Yield ◽

Fluorescence Properties ◽

Electron Donating Groups ◽

Phenyl Moiety

A study of fluorescence properties of thiazolo[4,5-b]pyrazine derivatives with the phenyl group at C2, prepared from amidopyrazines. The introduction of electron-donating groups onto the 2-phenyl moiety increases the fluorescence yield and appearance of solvatochromic character.

Download Full-text