1452922-06-3

Upstream product

• 151-10-0 1,3-Dimethoxybenzene 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 1452922-05-2 (2,6-dimethoxyphenyl)(2-methoxynaphthalen-1-yl)methanol 
• 1466-76-8 2-6-dimethoxybenzoic acid 

Downstream Products

• 1452922-07-4 (2-hydroxy-6-methoxyphenyl)(2-methoxynaphthalen-1-yl)methanone 
• 1452922-36-9 8,10-diphenyl-7,11-dipropyl-7,11-dihydrobenzo[a]benzo[5,6]quinolino[2,3,4-kl]acridin-17c-ylium tetrafluoroborate 
• 1452922-38-1 8,10-bis(phenylethynyl)-7,11-dipropyl-7,11-dihydrobenzo[a]benzo[5,6]quinolino[2,3,4-kl]acridin-17c-ylium tetrafluoroborate 

Relevant academic research and scientific papers

Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA+ and BDATA+, respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.

Physicochemical and Electronic Properties of Cationic [6]Helicenes: from Chemical and Electrochemical Stabilities to Far-Red (Polarized) Luminescence

The physicochemical properties of cationic dioxa (1), azaoxa (2), and diaza (3) [6]helicenes demonstrate a much higher chemical stability of the diaza adduct 3 (pKR+=20.4, (Formula presented.) =?0.72 V) compared to its azaoxa 2 (pKR+=15.2, (Formula presented.) =?0.45 V) and dioxa 1 (pKR+=8.8, (Formula presented.) =?0.12 V) analogues. The fluorescence of these cationic chromophores is established, and ranges from the orange to the far-red regions. From 1 to 3, a bathochromic shift of the lowest energy transitions (up to 614 nm in acetonitrile) and an enhancement of the fluorescence quantum yields and lifetimes (up to 31 % and 9.8 ns, respectively, at 658 nm) are observed. The triplet quantum yields and circularly polarized luminescence are also reported. Finally, fine tuning of the optical properties of the diaza [6]helicene core is achieved through selective and orthogonal post-functionalization reactions (12 examples, compounds 4–15). The electronic absorption is modulated from the orange to the far-red spectral range (560–731 nm), and fluorescence is observed from 591 to 755 nm with enhanced quantum efficiency up to 70 % (619 nm). The influence of the peripheral auxochrome substituents is rationalized by first-principles calculations.

Modular synthesis, orthogonal post-functionalization, absorption, and chiroptical properties of cationic [6]helicenes

Pick and choose: Novel cationic diaza-, azaoxo-, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross-coupling, or condensat