Far-Red to Near Infrared Emissive Aqueous Nanoparticles Based on a New Organic Material with Three BODIPY Dyes at the Periphery of the Core: A Combined Experimental and Theoretical Study

Benedetta M Squeo,Aristea Pavlou,Vasilis G Gregoriou,Alkmini D Nega,Panagiota Koralli,Andriana Schiza,Antonia Dimitrakopoulou-Strauss,Christos L Chochos,Aggelos Avramopoulos,Michael G Siskos

doi:10.3390/electronicmat2010003

Abstract

A new organic material with three 4,4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene dyes (BODIPYs) at the periphery of the central core is successfully synthesized (3BDP3T) and its corresponding aqueous nanoparticles are prepared via the encapsulation approach and characterized in detail both experimentally and theoretically with the aid of the Density Functional Theory (DFT). The linear and non-linear optical properties of the synthesized material are also studied. Until now, the development of organic materials with three BODIPYs as substituents is limited and their properties are not fully resolved. The obtained 3BDP3T-based nanoparticles exhibit far-red and near infrared (NIR) emission with photoluminescence quantum yields of 0.021, which is promising as a new fluorescent contrast agent in the far-red and NIR spectral regions.

Highlights

Acceptor-Donor-Acceptor (ADA) organic electronic materials are a class of functional dyes that provided the largest impact to the field of organic electronics and, especially, the small molecule-based organic photovoltaics (OPV) materials during the last five years [1,2,3,4,5].According to this concept, an electron-donating conjugated oligomer is functionalized at its ends with two electron-deficient units among which dicyanovinylene groups are the most widely utilized [6]
In this contribution, we present the successful synthesis and pr results, we were interested in exploring alternative chemical approaches, such as going characterization a new organic material of three beyond the classicalof type organic electronic electronic materials, byconsisting functionalizing electron the periphery of the benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene
Between the different fluorophores, BODIPYs are the most popular group. Their efficiency of the high photostability, sharp absorption and emission patterns, high fluorescence quantum yields, and high extinction coefficients makes them perfect candidates for bioimaging [7,19]. In this contribution, we present the successful synthesis and properties characterization of a new organic electronic material consisting of three BODIPY dyes at the periphery of the benzo[1,2-b:3,4-b0 :5,6-b”]trithiophene (3BDP3T; Figure 1) for the first time

Summary

Introduction

Acceptor-Donor-Acceptor (ADA) organic electronic materials are a class of functional dyes that provided the largest impact to the field of organic electronics and, especially, the small molecule-based organic photovoltaics (OPV) materials during the last five years [1,2,3,4,5] According to this concept, an electron-donating conjugated oligomer is functionalized at its ends with two electron-deficient units among which dicyanovinylene groups are the most widely utilized [6]. Stronger heterocyclic acceptors were originally utilized less frequently despite their beneficial influence on the absorption properties, i.e., reducing the band gap and increasing the color tunability Such a heterocyclic electron withdrawing the building block is the 4,4-difluoro-4-borata3a-azonia-4a-aza-s-indacene dye, which is more commonly known as BODIPY.

Methods

Results

Conclusion