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Effects of the alkyl group in (dialkylamino) perfluorophenazines on the melting point and fluorescence properties

机译：（二烷基氨基）全氟吩嗪中的烷基对熔点和荧光性质的影响

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摘要

The alkyl groups in 2-(dialkylamino)- and 2,7-bis(dialkylamino)perfluorophenazines drastically affected the melting point and solid-state fluorescence. 2-(Dialkylamino)- and 2,7-bis(dialkylamino) derivatives such as 2-(dioctylamino)-, 2-(didodecylamino)-, and 2,7-bis(dioctylamino)perfluorophenazines were liquid at ambient temperature, whereas shorter and longer dialkylamino derivatives were solid. 2-(Dioctadecylamino)perfluorophenazine exhibited a fluorescence maximum at 581 nm, being significantly blue-shifted compared with the other derivatives, with the most intense fluorescence quantum yield of 0.29 in the crystalline form. This result is attributed to the isolated dimer-type packing coming from long octadecyl groups. 2-(Dimethylamino)perfluorophenazine showed positive fluorescence solvatochromism due to a large dipole moment in the excited state. The computational analysis of (2-(dimethylamino)perfluorophenazine suggests that the red-shift of the fluorescence maximum in the crystalline form, compared with that in solution, mainly comes from pi-pi interactions with adjacent molecules. The fluorescence lifetime of 2-(dioctadecylamino)perfluorophenazine was significantly longer compared with 2-(dioctadecylamino)phenazine owing to the aromatic C-F bonds.
机译：2-（二烷基氨基）-和2,7-双（二烷基氨基）全氟吩嗪中的烷基极大地影响了熔点和固态荧光。 2-（二烷基氨基）-和2,7-双（二烷基氨基）衍生物，例如2-（二辛基氨基）-，2-（二十二烷基氨基）-和2,7-双（二辛基氨基）全氟吩嗪在室温下呈液态，而较短和更长的二烷基氨基衍生物是固体。 2-（二十八烷基氨基）全氟吩嗪在581 nm处显示最大荧光，与其他衍生物相比显着蓝移，晶体形式的荧光量子产率最高，为0.29。该结果归因于来自长十八烷基的分离的二聚体型堆积。 2-（二甲基氨基）全氟吩嗪由于在激发态具有较大的偶极矩而显示出正的荧光溶剂变色。 （2-（二甲基氨基）全氟吩嗪的计算分析表明，与溶液相比，晶体中荧光最大值的红移主要来自与相邻分子的pi-pi相互作用。2-（荧光寿命与2-（二十八烷基氨基）吩嗪相比，由于芳族CF键，二十八烷基氨基）全氟吩嗪明显更长。

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