Synthesis, structure and photophysical properties of regioisomeric sulfone-bridged pyrene–thienoacenes

Zhang, Shiqian; Chen, Ying; Liu, Zhi Qiang; Fang, Qi

doi:10.1016/j.jphotochem.2015.06.003

Cited by 7 publications

(1 citation statement)

References 16 publications

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“…For instance, Liu, Li et al developed regioisomeric sulfur-ands ulfonyl-bridged phenylpyrenes with optoelectronic properties that are highly dependent on the regiochemistry. [8] Similarly,H issler reported on the synthesis and photophysical properties of regioisomeric pyrene-benzo [b]phosphole and benzo [b]silole derivatives through metal catalyzed CÀHb ond activation. [9] The doping or substitution with electron-deficient boron atoms is also attractive because it typically reduces the LUMO energy of PAHs, therebye nhancing the acceptor character and shiftingt he absorptions and emissions to lower energies.…”

Section: Introductionmentioning

confidence: 99%

Controlling the Optoelectronic Properties of Pyrene by Regioselective Lewis Base‐Directed Electrophilic Aromatic Borylation

Vanga

Lalancette

Jäkle

2019

Chemistry A European J

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Given that pyrene represents one of the most versatile chromophores, the development of new selective routes for its functionalization and tuning of its emission properties is highly desirable. Pyrene‐based BN Lewis pair (LP)‐functionalized polycyclic aromatic hydrocarbons (PAHs) were prepared by regioselective Lewis base‐directed electrophilic aromatic substitution. The requisite 1,6‐dipyridylpyrene ligands were accessed by Suzuki–Miyaura cross‐coupling of 1,6‐bis(pinacolatoboryl)pyrenes with 2‐bromopyridine derivatives. Subsequent electrophilic borylation with BCl3 in the presence of AlCl3 and 2,6‐di‐tert‐butylpyridine as a hindered base produced the dichloroborane complexes, which were then in situ reacted with diphenyl or diethyl zinc. The presence or absence of alkyl chains in the 3,8‐positions of the pyrene moiety determined the position of the B−C bond formation (2,7 in the non‐K region versus 5,10 in the K region) and thereby also the size of the BN heterocycle (five‐ versus six‐membered). The impact of the regioisomeric borylation on the electrochemical, photophysical and structural properties was investigated and the conclusions supported by theoretical calculations. The rapid synthesis of derivatives that are borylated in the K region also suggests strong potential for the development of pyrene derivatives that are otherwise difficult to access.

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Section: Introductionmentioning

confidence: 99%