Wössner Jan S, Kohn Julia, Wassy Daniel, Hermann Mathias, Grimme Stefan, Esser Birgit
Institute for Organic Chemistry, University of Freiburg, Albertstraße 21, 79104 Freiburg, Germany.
Mulliken Center for Theoretical Chemistry (MCTC), University of Bonn, Beringstraße 4, 53115 Bonn, Germany.
Org Lett. 2022 Feb 4;24(4):983-988. doi: 10.1021/acs.orglett.1c03900. Epub 2022 Jan 14.
Conjugated nanohoops incorporating nonalternant hydrocarbons have altered optoelectronic properties compared to []cycloparaphenylenes or other purely aromatic hoops. We synthesized []cyclo-1,5-dibenzopentalenes ( = 4, 5), in which nonalternant dibenzo[,]pentalenes are connected through their pentalene units. This leads to an increase in antiaromatic character and low-lying LUMO energies. Calculations show puckered or entangled conformations of the precursor macrocyclic Pt-complexes. Our study proves dibenzopentalene as a versatile nonalternant building block for conjugated nanohoops with modifiable antiaromaticity and optoelectronic properties.
与[环对亚苯基]或其他纯芳香族环相比，含有非交替烃的共轭纳米环具有改变的光电性质。我们合成了[环-1,5-二苯并戊搭烯]( = 4, 5)，其中非交替的二苯并[,]戊搭烯通过它们的戊搭烯单元相连。这导致反芳香性增加和低LUMO能量。计算表明前体大环铂配合物具有褶皱或缠结的构象。我们的研究证明二苯并戊搭烯是一种通用的非交替构建单元，可用于具有可修饰反芳香性和光电性质的共轭纳米环。
