Short axially asymmetrically 1,3-disubstituted pyrene-based color-tunable emitters: Synthesis, characterization and optical properties

Wang, Chuan‐Zeng; Pang, Zijin; Yu, Ze-Dong; Zeng, Zhao-Xuan; Zhao, Wenxuan; Zhou, Ziyan; Redshaw, Carl; Yamato, Takehiko

doi:10.1016/j.tet.2020.131828

Cited by 11 publications

(8 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The series of compounds 2a-f was synthesized from 7-tert-butyl-1-bromopyrene 1 [54] with the corresponding aryl alkyne by a Sonogashira coupling reaction.…”

Section: Synthesis Of Compounds 2a-fmentioning

confidence: 99%

Pyrene-fused hexaarylbenzene luminogens: Synthesis, characterization, and aggregation-induced emission enhancement

Wang

Zhao

et al. 2021

Dyes and Pigments

Self Cite

View full text Add to dashboard Cite

“…The series of compounds 2a-f was synthesized from 7-tert-butyl-1-bromopyrene 1 [54] with the corresponding aryl alkyne by a Sonogashira coupling reaction.…”

Section: Synthesis Of Compounds 2a-fmentioning

confidence: 99%

Pyrene-fused hexaarylbenzene luminogens: Synthesis, characterization, and aggregation-induced emission enhancement

Wang

Zhao

et al. 2021

Dyes and Pigments

Self Cite

View full text Add to dashboard Cite

“…25 This is mainly due to its advantages, such as being solution processable, having a high thermal stability, enhanced charge carrier mobility high luminescence efficiency and also being amenable to controllable regioselective functionalization. [26][27][28] However, attributed due to the face-to-face interactions possible between the planar pyrene moieties, aggregation-caused quenching (ACQ) occurs due to formation of pyrene dimeric/excimeric emission in the aggregated state. 29 This shortcoming has limited high-technology applications of pyrene in the aggregated or solid state.…”

Section: Introductionmentioning

confidence: 99%

Substituent effects on the intermolecular interactions and emission behaviors in pyrene-based mechanochromic luminogens

Dong

Cao

et al. 2022

J. Mater. Chem. C

Self Cite

View full text Add to dashboard Cite

show abstract

“… 44 − 47 In fact, substituted pyrenes may display bathochromically shifted emission bands and largely elevated quantum yields. 48 , 49 Therefore, they have become prominent target structures for a variety of applications in materials science. 50 − 54 …”

Section: Introductionmentioning

confidence: 99%

BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State

et al. 2022

View full text Add to dashboard Cite

Boron–nitrogen substitutions in polycyclic aromatic hydrocarbons (PAHs) have a strong impact on the optical properties of the molecules due to a significantly more heterogeneous electron distribution. However, besides these single-molecule properties, the observed optical properties of PAHs critically depend on the degree of intermolecular interactions such as π–π-stacking, dipolar interactions, or the formation of dimers in the excited state. Pyrene is the most prominent example showing the latter as it exhibits a broadened and strongly bathochromically shifted emission band at high concentrations in solution compared to the respective monomers. In the solid state, the impact of intermolecular interactions is even higher as it determines the crystal packing crucially. In this work, a thiophene-flanked BN-pyrene ( BNP ) was synthesized and compared with its all-carbon analogue ( CCP ) in solution and in the solid state by means of crystallography, NMR spectroscopy, UV–vis spectroscopy, and photoluminescence (PL) spectroscopy. In solution, PL spectroscopy revealed the solvent-dependent presence of excimers of CCP at high concentrations. In contrast, no excimers were found in BNP . Clear differences were also observed in the single-crystal packing motifs. While CCP revealed overlapped pyrene planes with centroid distances in the range of classical π-stacking interactions, the BNP scaffolds were displaced and significantly more spatially separated.

show abstract

Short axially asymmetrically 1,3-disubstituted pyrene-based color-tunable emitters: Synthesis, characterization and optical properties

Cited by 11 publications

References 34 publications

Pyrene-fused hexaarylbenzene luminogens: Synthesis, characterization, and aggregation-induced emission enhancement

Pyrene-fused hexaarylbenzene luminogens: Synthesis, characterization, and aggregation-induced emission enhancement

Substituent effects on the intermolecular interactions and emission behaviors in pyrene-based mechanochromic luminogens

BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State

Contact Info

Product

Resources

About