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Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units
Author(s) -
Adachi Yohei,
Nabeya Taishi,
Kawakami Keigo,
Yamaji Kosuke,
Jäkle Frieder,
Ohshita Joji
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004643
Subject(s) - intramolecular force , boron , conjugated system , borane , stille reaction , boranes , palladium , materials science , germanium , crystal structure , crystallography , chemistry , photochemistry , stereochemistry , polymer , organic chemistry , catalysis , silicon
The introduction of unconventional elements into π‐conjugated systems has been studied to manipulate the electronic states and properties of compounds. Herein, boron‐ and germanium‐containing hybrid macrocycles, as a new class of element‐hybrid conjugated systems, have been synthesized. The palladium‐catalyzed Stille cross coupling of bis(bromothienyl)borane and bis(trimethylstannylthienyl)‐ or bis(trimethylstannylphenyl)‐substituted dithienogermoles as the boron‐ and germanium‐containing building blocks, respectively, produced a mixture of several macrocyclic compounds. Single‐crystal X‐ray analysis of the 2:2 coupling product revealed a planar structure with a cavity inside the macrocycle. The optical properties of the macrocyclic products indicated rather small electronic interactions between the building units. However, intramolecular photoenergy transfer from the dithienogermole unit to the boron unit was clearly observed with respect to the fluorescence spectra.