BNB-Doped
Phenalenyls: Modular Synthesis, Optoelectronic
Properties, and One-Electron Reduction
Posted on 2020-06-15 - 15:11
A highly modular
synthesis of BNB- and BOB-doped phenalenyls is
presented. Treatment of the 1,8-naphthalenediyl-bridged boronic acid
anhydride 1 with LiAlH4/Me3SiCl
afforded the corresponding 1,8-naphthalenediyl-supported diborane(6) 2, which served as the starting material for all subsequent
transformations. Upon addition of MesMgBr/Me3SiCl, 2 was readily converted to the tetraorganyl diborane(6) 5. The further heteroatoms were finally introduced through
the reaction of 2 with (Me3Si)2NR′ or 5 with H2NR′ or H2O (R′ = H, Me, p-Tol). A helically
twisted, fully BNB-embedded PAH 11 was prepared by combining 2 with a dibrominated m-terphenylamine, followed
by a Grignard-mediated double ring-closure reaction. All compounds
devoid of B–H bonds show favorable optoelectronic properties,
such as luminescence and reversible reduction behavior. In the case
of the BNB-phenalenyl 7 (BMes, NMe), the radical-anion
salt K[7•] was generated through chemical
reduction with K metal and characterized by EPR spectroscopy. K[7•] is not long-term stable in a THF/c-hexane solution, but abstracts an H atom with formation
of the diamagnetic BNB-doped 1H-phenalene K[7H].
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Scholz, Alexander
S.; Massoth, Julian G.; Bursch, Markus; Mewes, Jan-M.; Hetzke, Thilo; Wolf, Bernd; et al. (2020). BNB-Doped
Phenalenyls: Modular Synthesis, Optoelectronic
Properties, and One-Electron Reduction. ACS Publications. Collection. https://doi.org/10.1021/jacs.0c03118
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AUTHORS (10)
AS
Alexander
S. Scholz
JM
Julian G. Massoth
MB
Markus Bursch
JM
Jan-M. Mewes
TH
Thilo Hetzke
BW
Bernd Wolf
MB
Michael Bolte
HL
Hans-Wolfram Lerner
SG
Stefan Grimme
MW
Matthias Wagner
KEYWORDS
3 SiH atomTHFterphenylaminetransformationmaterialcompoundoptoelectronic propertiesMesMgBrnaphthalenediyl-bridged3 SiClbondEPR spectroscopyBMeacidGrignard-mediatedhelicallyanhydridehexane solutionformationdiboraneToldibrominated mNRnaphthalenediyl-supportedH 2 Oring-closure reactionBOB-doped phenalenylsheteroatomdiamagnetic BNB-doped 1 Htetraorganylchemical reductionBNB-phenalenyl 7synthesisabstractBNB-Doped PhenalenylsLiAlHK metalphenaleneOne-Electron ReductionBNB-embedded PAH 11radical-anionOptoelectronic Propertiesluminescencereduction behaviorModular SynthesisNMeboronic