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首页> 外文期刊>The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory >Solvatochromism of a novel betaine dye derived from purine
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Solvatochromism of a novel betaine dye derived from purine

机译：一种新型的嘌呤甜菜碱染料的溶剂变色

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摘要

A novel solvatochromic betaine dye has been synthesized from xanthosine and characterized spectroscopically by UV-vis in a broad range of solvents. The dye 9-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)-2-(pyridinium-1-yl)-9H-purin-6-olate, la, exhibits solvent-induced spectral band shifts that are (2)/(3) as large as that of the betaine known as Reichardt's dye, which forms the basis of the ET(30) solvent polarity scale. Moreover, the dye la is a ribonucleoside and hence has the potential application as a polarity probe for application in RNA oligonucleotides. The isomeric dye 6-(pyridinium-1)-yl-9H-purin-2-olate, 2a, has also been synthesized and exhibits slightly smaller solvatochromic band shifts. The new betaine dyes have also been studied by comparing the experimental and calculated solvatochromic shifts based on the calculation of the UV/vis absorption spectra, using a combination of methods with density functional theory (DFT). The COSMO continuum dielectric method, an applied electric field term in the Hamiltonian, and time-dependent density functional theory (TDDFT) methods were used to obtain absorption energies, ground-state dipole moments, and the difference dipole moment between the ground and excited states. The calculations predict a lower energy absorption band of charge-transfer character that is highly solvatochromic, and a higher energy absorption band that has pi-pi* character which is not solvatochromic, in agreement with the experimental data. For Reichardt's dye the difference dipole moment between the ground and excited state (Deltamu = mu(e) - mu(g)) was also calculated and compared to experiment: Deltamu(calcd) = -6 D and Deltamu(exptl) = -9 +/- 1 D.(1) The ground-state dipole moment was found to be mu(g)(calcd) = 18 D and mu(g)(exptl) = 14.8 +/- 1.2 D.(1)
机译：一种新的溶剂化变色甜菜碱染料是由黄嘌呤合成的，并通过紫外可见光谱在各种溶剂中进行表征。染料9-（2'，3'，5'-三-O-乙酰基-β-D-呋喃呋喃糖基）-2-（吡啶-1-基）-9H-嘌呤-6-油酸酯1a显示溶剂为诱导的光谱带位移为甜菜碱（被称为莱卡德染料）的（2）/（3）大，这形成了ET（30）溶剂极性标度的基础。而且，染料Ia是核糖核苷，因此具有潜在的应用作为在RNA寡核苷酸中应用的极性探针。异构染料6-（吡啶鎓-1）-基-9H-嘌呤-2-油酸酯2a也已经合成，并且表现出稍小的溶剂化变色带移。还通过结合使用密度泛函理论（DFT）的方法，通过计算UV / vis吸收光谱，比较了实验值和计算得出的溶剂化色移，对新型甜菜碱染料进行了研究。使用COSMO连续介质法，哈密顿方程中的施加电场项以及时变密度泛函理论（TDDFT）方法来获得吸收能，基态偶极矩以及基态和激发态之间的差分偶极矩。计算结果与实验数据相一致，预测出具有高溶剂变色性的电荷转移特征的较低能量吸收带和具有非溶剂变色性的pi-pi *特征的较高能量吸收带。对于Reichardt染料，还计算了基态和激发态之间的偶极矩差（Deltamu = mu（e）-mu（g））并与实验进行了比较：Deltamu（calcd）= -6 D和Deltamu（exptl）= -9 +/- 1 D.（1）发现基态偶极矩为mu（g）（计算）= 18 D和mu（g）（exptl）= 14.8 +/- 1.2 D.（1）

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