Tailoring the Photophysical Signatures of BODIPY Dyes: Toward Fluorescence Standards across the Visible Spectral Region

Rebeca Sola Llano,César Fernando Azael Gómez Durán,Iñigo López Arbeloa,Edurne Avellanal Zaballa,Eduardo Peña Cabrera,Jorge Bañuelos,José Luis Belmonte Vázquez

doi:10.5772/intechopen.74848

Abstract

The modern synthetic routes in organic chemistry, as well as the recent advances in high-resolution spectroscopic and microscopic techniques, have awakened a renewable interest in the development of organic fluorophores. In this regard, boron-dipyrrin (BODIPY) dyes are ranked at the top position as luminophores to be applied in photonics or biophotonics. This chromophore outstands not only by its excellent and tunable photophysical signatures, but also by the chemical versatility of its core, which is readily available to a myriad of functionalization routes. In this chapter, we show that, after a rational design, bright and photostable BODIPYs can be achieved along the whole visible spectral region, being suitable as molecular probes or active media of lasers. Alternatively, the selective functionalization of the dipyrrin core, mainly at meso position, can induce new photophysical phenomena (such as charge transfer) paving the way to the development of fluorescent sensors, where the fluorescent response is sensitive to a specific environmental property.

Highlights

The recent advances in high-resolution fluorescence microscopy have played a key role in the success and boom of bioimaging techniques in the last few years
Boron-dipyrromethene (BODIPY) dyes are likely at the “pole” position, owing to their excellent photophysical signatures [8, 9], but mainly due to the chemical versatility of its boron-dipyrrin core, ready available to a multitude of synthetic routes (Figure 1) [10, 11]
Fluorescent probes and laser dyes based on BODIPY can be attained covering the whole visible spectral region just choosing the adequate substitution pattern at the right chromophoric position

Summary

Introduction

The recent advances in high-resolution fluorescence microscopy have played a key role in the success and boom of bioimaging techniques in the last few years. Thanks to super resolution microscopy (nanoscopy, awarded with the Nobel Prize of 2014 in chemistry), the diffraction resolution limit is surpassed, allowing the detection at the single molecular level [1–3] The development of this revolutionary technological tool has awakened a renewed interest in the design of organic luminophores with improved properties as fluorescent probes or markers to detect or monitor biochemical events [4]. We highlight some structural guidelines to shift the spectral bands to both edges (blue and red) of the visible spectral region, while keeping their characteristic high fluorescent efficiencies In this way, fluorescent probes and laser dyes based on BODIPY can be attained covering the whole visible spectral region just choosing the adequate substitution pattern at the right chromophoric position. The fluorescent efficiency can response selectively to a specific property of the surrounding environment (such as polarity and acidity/basicity) leading to fluorescent sensors [23–25]

Modulation of the spectral shift

Red-emitting BODIPYs

Induction of new photophysical processes

Sensor of polarity

Findings

Conclusions