N,S-heterocyclic carbene containing benzothiazol-2-ylidene-Ru(II) and Pd (II) new complexes functionalized with butyl linked carbazole moiety: Synthesis, characterization and their catalytic efficiency and electropolymerizations

Karakas H., Guzel M., AK M., KILINÇARSLAN R., Özdemir N.

EUROPEAN POLYMER JOURNAL, cilt.181, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 181
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.eurpolymj.2022.111630
  • Dergi Adı: EUROPEAN POLYMER JOURNAL
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, PASCAL, Aerospace Database, Chemical Abstracts Core, Communication Abstracts, INSPEC, Metadex, Civil Engineering Abstracts
  • Anahtar Kelimeler: N,S-heterocyclic carbene, Benzothiazole-2-ylidene, Benzothiazolium salt, Solvent-free alkylation, Electropolymerization, Carbazole, Catalyst, Carbene precursor, N-HETEROCYCLIC CARBENES, SUZUKI-MIYAURA, BENZOTHIAZOLIN-2-YLIDENE COMPLEXES, PALLADIUM PRECATALYST, (NHC)PD(ALLYL)CL NHC, CONDUCTING POLYMER, COUPLING REACTIONS, BUCHWALD-HARTWIG, PD(II) COMPLEXES, GLUCOSE-OXIDASE
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In contrast to the large number of polymeric N-heterocyclic carbenes (NHCs) there are relatively few examples of NHCs-containing conductive polymers. However, conducting polymers (CPs) could be excellent hosts for NHC compounds, as they can easily form polymer films electrochemically, and their optical & electrical properties can be easily tuned by electrochemically or changing bonding groups in their structure. In this work, the N,S-heterocyclic carbene (NHC) ligand precursor, N-(4-butylcarbazole)benzothiazolium bromide (1) was prepared by solvent-free alkylation of benzothiazole by 9-(4-bromobutyl)carbazole with high efficiency. The air- and moisture-stable new piano-stool Ru(II)-N,S-NHC (2) and PEPPSI type Pd(II)-N,S-NHC (3) complexes, were synthesized and characterized by H-1- and C-13 NMR, FT-IR, UV-vis and ESI-MS spectroscopic methods and elemental analysis. Further confirmations of structural details for benzothiazolium salt (1) and its Ru(II)-N,S-NHC complex (2) were determined by X-ray single-crystal diffraction. The catalytic performance of the complexes (2 and 3) in transfer hydrogenation (TH) of acetophenone and Suzuki-Miyaura cross-coupling reactions of aryl bromides were also investigated, respectively. All compounds (1-3) were electrochemically polymerized and conducting polymer films with pendant carbene complex moieties were obtained. The electrical and optical properties of the resulting polymers were characterized via spectroelectrochemical studies.