Unpredicted Concentration-Dependent Sensory Properties of Pyrene-Containing NBN-Doped Polycyclic Aromatic Hydrocarbons.

Hang Xiao,Qingrong Qian,Wen-Ming Wan,Xiao-Li Sun,Hongli Bao,Qinghua Chen,Tao Li

doi:10.3390/molecules27010327

Abstract

Pyrene molecules containing NBN-doped polycyclic aromatic hydrocarbons (PAHs) have been synthesized by a simple and efficient intermolecular dehydration reaction between 1-pyrenylboronic acid and aromatic diamine. Pyrene-B (o-phenylenediamine) with a five-membered NBN ring and pyrene-B (1,8-diaminonaphthalene) with a six-membered NBN ring show differing luminescence. Pyrene-B (o-phenylenediamine) shows concentration-dependent luminescence and enhanced emission after grinding at solid state. Pyrene-B (1,8-diaminonaphthalene) exhibits a turn-on type luminescence upon fluoride ion addition at lower concentration, as well as concentration-dependent stability. Further potential applications of Pyrene-B (o-phenylenediamine) on artificial light-harvesting film were demonstrated by using commercial NiR dye as acceptor.

Highlights

IntroductionBoron has received exceptional attention because of its unique photophysical and redox properties [1–5]
To verify the physical concentration strategy to stabilize boron-doped π-systems, the pyrene moiety was molecularly designed in the NBN-doped polycyclic aromatic hydrocarbons (PAHs) as shown in Scheme 1
(1,2-diaminobenzene) (Py-NBN-Ph) with a five-membered NBN ring and pyrene-B (1,8diaminonaphthalene) (Py-NBN-Naphth) with a six-membered NBN ring were synthesized with a yield of 94% and 95%, respectively

Summary

Introduction

Boron has received exceptional attention because of its unique photophysical and redox properties [1–5]. Boron-doped π-systems have received special attentions because of their desirable and potential optical, electronic and sensory properties [6–9]. Compared with the corresponding all-carbon analogues, organic π-conjugated compounds with a novel BN bond usually have distinct optoelectronic properties/advantages due to the empty p-orbital of the boron center [15–17]. Considerable progress has been made on the comprehensive synthesis of BN- and BNB-doped π-systems with outstanding photophysical properties by pioneering researchers such as Dewar, White, Ashe, Liu, Braunschweig, Schäfer and Jäkle, etc. These outstanding BN- and BNB-doped π-systems suffer from synthesis methods involving rigorous reaction conditions (e.g., air and/or moisture free), multiple steps and unsatisfied total yield [33–38]

Methods

Results

Conclusion