Synthesis and Halochromic Properties of 1,2,6-Tri- and 1,2,3,6-Tetra-aryl Azulenes,ChemPlusChem

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Synthesis and Halochromic Properties of 1,2,6-Tri- and 1,2,3,6-Tetra-aryl Azulenes
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-07-27 , DOI: 10.1002/cplu.202100261
Qiang Zhu ₁ , Zhuang Mao Png ₁ , Tingting Lin ₁ , Xian Jun Loh ₁ , Tao Tang ₁ , Jianwei Xu _{1,

2}

Affiliation

A series of novel 2,6-functionalized azulene molecules Azu1-3 with varied fluorene substituents at the 1- and 3-positions of azulene as well as at the 5’-position of 2-thiophene group were synthesized. Their electronic absorption and emission spectra at neutral and protonated states were examined. It was found that after functionalization with fluorenyl groups, Azu1-3 exhibited absorption maxima at 445, 451 to 468 nm, respectively. In contrast, their corresponding protonated species showed much redshifted absorption maxima at 560, 582 to 643 nm, respectively, mainly due to the extension of conjugation length and the large dipole moment along the C_2v axis of 2,6-substituted azulene molecules. Azu1-3 are non-fluorescent in their neutral forms, but became emissive in their protonated states. Analysis of absorption and emission spectra shows that substitution of the 1- or 3-position of azulene led to decrease in response to trifluoroacetic acid.

中文翻译：

1,2,6-三和 1,2,3,6-四芳基甘菊烯的合成和卤致变色性能

合成了一系列新型2,6-功能化的薁分子Azu1-3，其在薁的1-和3-位以及2-噻吩基团的5'-位具有不同的芴取代基。检查了它们在中性和质子化状态下的电子吸收和发射光谱。发现用芴基官能化后，Azu1-3 分别在445、451至 468 nm 处表现出最大吸收。相比之下，它们相应的质子化物质分别在 560、582 至 643 nm 处显示出很大的红移吸收最大值，这主要是由于共轭长度的延长和2,6-取代的 azulene 分子沿 C _2v轴的大偶极矩。阿祖1-3在中性形式下是非荧光的，但在质子化状态下会发光。吸收和发射光谱分析表明，薁的 1 位或 3 位取代导致对三氟乙酸的响应降低。

更新日期：2021-08-17

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