Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units. Issue 10 (2nd February 2021)

• Record Type: Journal Article
• Authors: Adachi, Yohei; Nabeya, Taishi; Kawakami, Keigo; Yamaji, Kosuke; Jäkle, Frieder; Ohshita, Joji
• Is Part Of: Chemistry. Volume 27:Issue 10(2021)
• Page Start: 3306
• Page End: 3314
• Publication Date: 2021-02-02
• Subjects: boron -- energy transfer -- germoles -- hybrid materials -- macrocycles; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004643
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Unconventional elements : New macrocyclic compounds containing tricoordinate boron and germanium show characteristic fluoride responses in their optical properties, depending on their structures. This indicates that the element‐hybrid macrocyclic system is promising as a new class of fluoride sensor material.