Towards Efficient and Photostable Red‐Emitting Photonic Materials Based on Symmetric All‐BODIPY‐Triads, ‐Pentads, and ‐Hexads

Abstract

The development of efficient and stable red and near‐IR emitting materials under hard radiation doses and/or prolonged times is a sought‐after task due to their widespread applications in optoelectronics and biophotonics. To this aim, novel symmetric all‐BODIPY‐triads, ‐pentads, and ‐hexads have been designed and synthesized as light‐harvesting arrays. These photonic materials are spectrally active in the 655–730 nm region and display high molar absorption across UV–visible region. Furthermore, they provide, to the best of our knowledge, the highest lasing efficiency (up to 68 %) and the highest photostability (tolerance >1300 GJ mol−1) in the near‐IR spectral region ever recorded under drastic pumping conditions. Additionally, the modular synthetic strategy to access the cassettes allows the systematic study of their photonic behavior related to structural factors. Collectively, the outstanding behavior of these multichromophoric photonic materials provides the keystone for engineering multifunctional systems to expedite the next generation of effective red optical materials.

Unravelling the excited state dynamics of monofunctionalized mono- and distyryl-BODIPY and perylenediimide dyads

“…Since the spatial disposition of molecular entities always has an impact on the energy/electron transfer dynamics in such cassettes, b-substitution seems to be of interest although only one report on a cassette of b-disubstituted STBDP with BODIPY is known. 49 Here, we report the synthesis and exploration of the photophysics of new monofunctionalized monostyryl and distyryl-BODIPY and their resultant dyads 1 and 2 with PDIs synthesized in a way that the PDI substitutions were performed at only one of the b-positions of the mono-and distyryl-BODIPYs. Even though combinations of BODIPY and PDI are reported in the context of artificial light harvesting cassette design, [50][51][52][53][54][55] to the best of our knowledge, STBDPs in combination with PDIs connected through b-positions have never been reported.…”

“…Since the spatial disposition of molecular entities always has an impact on the energy/electron transfer dynamics in such cassettes, β -substitution seems to be of interest although only one report on a cassette of β -disubstituted STBDP with BODIPY is known. 49…”

Koloratzaile fotoaktiboen belaunaldi berria

“…Hori lortzeko, π-hedatutako egitura duten BODIPYak aukeratu dira energia hartzaile eta igorle bezala (2. irudia, BB sistemak) [18]. Multikromoforoan jatorrizko BODIPYa aukeratu da energia emaile bezala, eta horrelako egitura berdinak erantsi zaizkio α-estirilBOIPYari (energia-hartzailea) beheko bi fenilo taldeetan (BB1 emaile/hartzaile erlazioa = 2/1).…”

“…Hortaz, antena hauetan detekzio eta kitzikapen eremuak oso urrun daude bata bestearengandik, interferentziak murriztuz eta fotoegonkortasuna handituz, kromoforo igorlea ez delako zertan zuzenki kitzikatu behar, baizik eta emailetik etor dakioke energia. Antenasistema artifizialek erabilera anitz aurkeztu ditzakete; hala nola, erdieroaleak aktibatzeko zelula fotovoltaikoetan, OLEDak garatzeko edota laserretan aplikatzeko [16][17][18]. Gainera, sistema multikromoforiko hauek moldakortasun handia azaltzen dute, horien diseinu eta sintesirako kromoforomota eta lotura-kokapen desberdinak aukeratu ahal direlako.…”

Access to 2,6-Dipropargylated BODIPYs as “Clickable” Congeners of Pyrromethene-567 Dye: Photostability and Synthetic Versatility

“…Finally, the modular use of dipropargyl BODIPYs 10a and 10b , in conjunction with azido-BODIPYs 20 and 21 , made possible the CuAAC-mediated assembly of isomeric all-BODIPY triads 22a,b and 23 , , where the donor (D) and acceptor (A) roles occupy alternate locations (i.e., A-D-A and D-A-D, respectively, Figure ). Distyryl BODIPYs 19 and 21 were uneventfully obtained by Knoevenagel condensation of propargyl BODIPY 10b and azido-BODIPY 20 , with benzaldehyde in DMF.…”