N-BODIPYs Come into Play: Smart Dyes for Photonic Materials

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Ray Leiva, César and Díaz Casado, Laura and Avellanal-Zaballa, Edurne and Bañuelos Prieto, Jorge and Cerdán Pedraza, Luis and García Moreno, Inmaculada and Moreno Jiménez, Florencio and Maroto, Beatriz Lora and López Arbeloa, Íñigo María and Moya Cerero, Santiago de la (2017) N-BODIPYs Come into Play: Smart Dyes for Photonic Materials. Chemistry: a european journal, 23 (39). pp. 9383-9390. ISSN 0947-6539(Print) 1521-3765 (On line)

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Official URL: https://doi.org/10.1002/chem.201701350



Abstract

N-BODIPYs (diaminoboron dipyrromethenes) are unveiled as a new family of BODIPY dyes with huge technological potential. Synthetic access to these systems has been gained through a judicious design focused on stabilizing the involved diaminoboron chelate. Once stabilized, the obtained N-BODIPYs retain the effective photophysical behavior exhibited by other boron-substituted BODIPYs, such as O-BODIPYs. However, key bonding features of nitrogen compared to those of oxygen (enhanced bond valence and different bond directionality) open up new possibilities forfunctionalizing BODIPYs, allowing an increase in the number of pendant moieties (from two in O-BODIPYs, up to four in N-BODIPYs) near the chromophore and, therefore, greater control of the photophysics. As a proof of concept, the following findings are discussed: (1) the low-cost and straightforward synthesis of a selected series of N-BODIPYs; (2) their outstanding photophysical properties compared to those of related effective dyes (excellent emission signatures, including fluorescence in the solid state; notable lasing capacities in the liquid phase and when doped into polymers; improved laser performance compared to the parent F-BODIPYs); (3) the versatility of the diaminoboron moiety in allowing the generation of multifunctionalized BODIPYs, permitting access to both symmetric and asymmetric dyes; (4) the capability of such versatility to finely modulate the dye photophysics towards different photonic applications, from lasing to chemosensing.


Item Type:Article
Additional Information:

Manuscript received: March 24, 2017; Accepted manuscript online: May 3, 2017; Version of record online: June 12, 2017

Uncontrolled Keywords:BODIPYs, Fluorescence, Lasers, Photophysics, Sensors
Subjects:Sciences > Physics > Optics
Sciences > Physics > Chemistry, Physical and theoretical
Sciences > Chemistry > Chemistry, Organic
ID Code:69778
Deposited On:27 Jul 2022 09:07
Last Modified:03 Aug 2022 10:50

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