Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Ghosh, Animesh; Budanović, Maja; Li, Tianjiao; Liang, Caihong; Klein, Maciej; Soci, Cesare; Webster, Richard D.; Gurzadyan, Gagik G.; Grimsdale, Andrew C.

doi:10.1002/ajoc.202100373

Cited by 8 publications

(14 citation statements)

References 69 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Density functional theory (DFT) calculations were performed to investigate the emission mechanism of the polymer, by comparing the monomers (N = 1) and polymers (N = 4). As shown in Figure 4 , all polymers show a lower band gap, resulting in the electron transition and luminescence as previously reported [ 44 , 45 , 46 , 47 ]. As shown in Figures S6–S8 and Table S1 (see Supplementary Materials) , the band gap decreases with the N increasing for all polymers.…”

Section: Resultssupporting

confidence: 80%

Novel NBN-Embedded Polymers and Their Application as Fluorescent Probes in Fe3+ and Cr3+ Detection

Sheng

Sun

et al. 2022

Polymers

View full text Add to dashboard Cite

The isosteric replacement of C═C by B–N units in conjugated organic systems has recently attracted tremendous interest due to its desirable optical, electronic and sensory properties. Compared with BN-, NBN- and BNB-doped polycyclic aromatic hydrocarbons, NBN-embedded polymers are poised to expand the diversity and functionality of olefin polymers, but this new class of materials remain underexplored. Herein, a series of polymers with BNB-doped π-system as a pendant group were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization from NBN-containing vinyl monomers, which was prepared via intermolecular dehydration reaction between boronic acid and diamine moieties in one pot. Poly{2-(4-Vinylphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine} (P1), poly{N-(4-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)phenyl)acrylamide} (P2) and poly{N-(4-(1H-benzo[d][1,3,2]diazaborol-2(3H)-yl)phenyl)acrylamide} (P3) were successfully synthesized. Their structure, photophysical properties and application in metal ion detection were investigated. Three polymers exhibit obvious solvatochromic fluorescence. As fluorescent sensors for the detection of Fe3+ and Cr3+, P1 and P2 show excellent selectivity and sensitivity. The limit of detection (LOD) achieved by Fe3+ is 7.30 nM, and the LOD achieved by Cr3+ is 14.69 nM, which indicates the great potential of these NBN-embedded polymers as metal fluorescence sensors.

show abstract

Section: Resultssupporting

confidence: 80%

Novel NBN-Embedded Polymers and Their Application as Fluorescent Probes in Fe3+ and Cr3+ Detection

Sheng

Sun

et al. 2022

Polymers

View full text Add to dashboard Cite

show abstract

“…5,14-Diphenylbenzo[j]naphtho[2,1,8-def][2,7]phenanthroline 5 a contains the structural features of 5,9-diphenyl-2-azapyrene (5,9-diphenylnaphtho[2,1,8-def]isoquinoline) [27] and 5-azatetracene (benzo[b]acridine). [63] Therefore, we compared the properties of these compounds (Figure 6). 5,9-Diphenyl-2-azapyrene lacks the annulated quinoline moiety in the K-region.…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

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

Mertz

Molenda

Boldt

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

A series of hitherto unknown 5,14‐diphenylbenzo[j]naphtho[2,1,8‐def][2,7]phenanthrolines, containing a 5‐azatetracene and a 2‐azapyrene subunit, were prepared by combination of Pd‐catalyzed cross‐coupling reactions with a one‐pot Povarov/cycloisomerization reaction. In the final key step four new bonds are formed in one step. The synthetic approach allows for a high degree of diversification of the heterocyclic core structure. The optical and electrochemical properties were studied experimentally and by DFT/TD‐DFT and NICS calculations. Due to the presence of the 2‐azapyrene subunit, the typical electronic nature and characteristics of the 5‐azatetracene moiety are lost and the compounds are electronically and optically more related to 2‐azapyrenes.

show abstract

“…Our dibenzodioxins look similar structurally to a number of known polycyclic and heterocyclic aromatic compounds like anthracene, [8a] tetracene, [8b] phenazine, [8c] phenothiazine, [8c] phenoxazine [8d] etc. whose redox properties have already been studied.…”

Section: Introductionmentioning

confidence: 66%

“…As seen from Figure 9, tetracene 5 shows single irreversible reduction peak at −2.15 V (vs Fc/Fc + ; Figure 9, structure 5) and first oxidation potential peak at +0.56 V (vs Fc/Fc + ; Figure 9, structure 5) [8b] . Introduction of nitrogen atoms in the ring system makes the oxidation harder as seen by comparing with our analogous compound 3 a (E oxd =+0.600 V vs Fc/Fc + ; table 1, entry no.…”

Section: Resultsmentioning

confidence: 90%

“…8) has a pyrazine ring, dicyano groups and also an additional nitro as EWG, which lowers the reduction potential to nearly half of tetracene 5 . When we compare compound 6 [8b] of Figure 9 with our compound 3 a (E red =−1.219 V vs Fc/Fc + ; table 1, entry no. 7), we infer that reduction is harder in 6 (E 1 red =−1.8 V vs Fc/Fc + ; Figure 9, structure 6) due to pyridine being weaker electron acceptor than pyrazine and also absence of dicyano units unlike 3 a .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

An Electrochemical Investigation into the Redox Properties of Push‐Pull Dibenzodioxins and Comparative Analysis with Analogous Heteroacenes

2022

View full text Add to dashboard Cite

A series of dibenzodioxins containing electron push-pull groups were synthesized using simple methods and their spectroscopic and redox behavior was studied. Electrochemical experiments were performed to measure the redox potentials of the substituted dibenzodioxins. The role of individual molecular subunits in tweaking the redox potential values was delineated by comparing them with the electrochemical properties of analogous heteroacenes. In many cases, our redox potentials were found to be comparably low with that of many wellknown heteroacenes.

show abstract

Synthesis of 5‐Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

Cited by 8 publications

References 69 publications

Novel NBN-Embedded Polymers and Their Application as Fluorescent Probes in Fe3+ and Cr3+ Detection

Novel NBN-Embedded Polymers and Their Application as Fluorescent Probes in Fe3+ and Cr3+ Detection

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

An Electrochemical Investigation into the Redox Properties of Push‐Pull Dibenzodioxins and Comparative Analysis with Analogous Heteroacenes

Contact Info

Product

Resources

About