Evolving Fluorophores into Circularly Polarized Luminophores with a Chiral Naphthalene Tetramer: Proposal of Excimer Chirality Rule for CPL,Journal of the American Chemical Society

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Evolving Fluorophores into Circularly Polarized Luminophores with a Chiral Naphthalene Tetramer: Proposal of Excimer Chirality Rule for CPL
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-04-05 , DOI: 10.1021/jacs.9b02582
Kazuto Takaishi _{1,

2} , Kazuhiro Iwachido ₁ , Ryosuke Takehana ₁ , Masanobu Uchiyama _{2,

3,

4} , Tadashi Ema ₁

Affiliation

A versatile method for converting various fluorescent polycyclic aromatic hydrocarbons into circularly polarized luminescence (CPL) excimer dyes with high glum and ΦFL values is reported. This method involves the functionalization of a chiral quaternaphthyl with six fluorophores via ester linkages in the last step of the synthesis. The usefulness of this approach was demonstrated for 1-, 2-, and 4-pyrenyl, 2- and 3-perylenyl, and 2-anthryl dyes. Most of them are the first or rare examples of CPL dyes. In the ground state, the fluorophores are tightly arranged by cumulative steric and electronic effects. In the excited state, the fluorophores form a twist excimer that maintains the ground-state conformations. The local chiral excimer directly affected the CPL properties. The systematic study on the signs of the CPLs allowed us to find a rule called the excimer chirality rule: right- and left-handed excimers exhibit (+)- and (-)-CPL, respectively.

中文翻译：

使用手性萘四聚体将荧光团进化为圆偏振发光团：CPL 准分子手性规则的提议

报告了一种将各种荧光多环芳烃转化为具有高 glum 和 ΦFL 值的圆偏振发光 (CPL) 准分子染料的通用方法。该方法涉及在合成的最后一步通过酯键用六个荧光团对手性季萘进行功能化。这种方法对 1-、2- 和 4-芘基、2- 和 3- 苝基以及 2-蒽基染料的有效性得到了证明。它们中的大多数是 CPL 染料的第一个或罕见的例子。在基态，荧光团通过累积空间和电子效应紧密排列。在激发态，荧光团形成扭曲准分子，维持基态构象。局部手性准分子直接影响 CPL 性能。

更新日期：2019-04-05

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