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@ARTICLE{Zender:611055,
author = {Zender, Elena and Valverde, Danillo and Neubaur, Robert and
Karger, Sebastian and Virovets, Alexandr and Bolte, Michael
and Lerner, Hans-Wolfram and Olivier, Yoann and Wagner,
Matthias},
title = {{B}orylation and rearrangement reactions of
azasilaanthracenes to afford {B},{N}-doped nanographenes},
journal = {Dalton transactions},
volume = {53},
number = {22},
issn = {1477-9226},
address = {London},
publisher = {Royal Society of Chemistry},
reportid = {PUBDB-2024-04817},
pages = {9294-9300},
year = {2024},
abstract = {An air-stable B3,N3-containing dibenzobisanthene (8) was
prepared in $29\%$ yield by heating a 1,3,5-tri(aza
silaanthryl)benzene (5) with BBr3 (180 °C). Under these
conditions, the reaction does not stop after three fold
SiMe2/BBr exchange but proceeds further via two
rearrangement and two intramolecular C–H borylation steps.
Some mechanistic details were unveiled by using smaller
model systems and applying lower reaction temperatures.
According to X-ray crystallography, compound 8 has a
helically distorted scaffold. Due to its multiple resonance
structure, it shows a narrow-band blue-green emission (λem
= 493 nm; ΦPL = $84\%;$ FWHM = 0.20 eV; THF); samples
measured in PMMA gave prompt and delayed fluorescence
lifetimes of 10.7 ns and 136 µs, respectively. The optical
properties of 8 and of structurally related species were
also investigated by quantum-chemical means: most of these
compounds exhibit a small energy gap ΔEST between the
lowest excited singlet (S1) and triplet (T1) states and a
non-negligible spin–orbit coupling (SOC) between S1 and
T1/T2, demonstrating their potential as thermally activated
delayed fluor escence (TADF) emitters},
cin = {DOOR ; HAS-User},
ddc = {540},
cid = {I:(DE-H253)HAS-User-20120731},
pnm = {6G3 - PETRA III (DESY) (POF4-6G3) / FS-Proposal: I-20220822
(I-20220822)},
pid = {G:(DE-HGF)POF4-6G3 / G:(DE-H253)I-20220822},
experiment = {EXP:(DE-H253)P-P24-20150101},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:38747255},
UT = {WOS:001222864400001},
doi = {10.1039/D4DT01166J},
url = {https://bib-pubdb1.desy.de/record/611055},
}