36044-42-5Relevant articles and documents
Ethynylazulenes - Building blocks for novel oligoazulenes with ethynyl and butadiynyl bridges
Fabian, Kai H. H.,Elwahy, Ahmed H. M.,Hafner, Klaus
, p. 791 - 802 (2006)
The azulenes 3a,b, 6a,b, 9, 12 and 15 ethynylated in the five-membered ring were prepared by Pd-catalysed cross-coupling of the corresponding iodoazulenes 1a,b, 4a,b, 7, 10 and 13, respectively, with trimethylsilylacetylene and subsequent desilylation. The synthesis of some acyclic oligomers 23-30, 32-36 and 38-40 from these ethynylazulenes could be accomplished by oxidative Eglinton coupling as well as Pd/Cu-catalysed cross-coupling reactions with the appropriate iodoazulenes 1a,b, 4b, 31 and 34. The UV/Vis spectra of the novel oligomers 32, 35 and 36 allow an estimation of the bandgap (Eg) of poly(1,3-azulenylethynylene)s lower than 2eV. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Azulene Bridged π-Distorted Chromophores: The Influence of Structural Symmetry on Optoelectrochemical and Photovoltaic Parameters
Murugan, Palanichamy,Praveen, Chandrasekar,Raheem, Abbasriyaludeen Abdul,Shanmugam, Ramasamy
, p. 1451 - 1460 (2021/11/03)
Conjugated chromophores possessing π-twisted functionality such as tetracyanobutadiene (TCBD) have emerged as promising active layer materials for organic photovoltaics (OPVs). In this study, we disclose the synthesis of two azulenyl chromophores containing one and two TCBD groups. The symmetrical and unsymmetrical structural characteristics of these molecules inflict dissimilar optoelectronic and electrochemical properties. Based on molar absorptivity, aggregation behavior, HOMO-LUMO energies and other quantum chemical parameters, the symmetrical molecule (TATC2) appears to be a better non-fullerene acceptor (NFA) compared to its unsymmetrical counterpart (TATC1). For instance, higher absorptivity and deeper HOMO-LUMO levels for TATC2 (23950 M?1 cm?1; ?6.01 eV/?3.86 eV) over TATC1 (12200 M1 cm?1; ?5.46 eV/?3.64 eV) was observed. Validating this structure-property relationship on solar cell prototypes exhibited higher photovoltaic parameters (VOC=0.54 V, FF=0.48, JSC=6.42 mA/cm2) for TATC2 than TATC1 (VOC=0.47 V, FF=0.38, JSC=5.77 mA/cm2). Though the device parameters are not high, this work uncovers the intrinsic properties of azulene-tethered twisted chromophores as potential π-semiconductor choice for NFA solar cells. In particular, this report explores the utility of azulene-based π-twisted semiconductors as acceptor material for OPVs with cell efficiencies of 1.70 and 1.04 % for TATC2 and TATC1 respectively.
An efficient and regioselective iodination of electron-rich aromatic compounds using N-chlorosuccinimide and sodium iodide
Yamamoto, Takuya,Toyota, Kozo,Morita, Noboru
experimental part, p. 1364 - 1366 (2010/05/03)
An efficient and regioselective method for iodination of electron-rich aromatic compounds was found using N-chlorosuccinimide and sodium iodide in AcOH with short reaction times. This method is also applicable to non-benzenoid aromatic or heteroaromatic c
