First Demonstration of the Applicability of the Latent Pigment Approach to Plastic Luminescent Solar Concentrators

Mattiello, Sara; Sanzone, Alessandro; Brazzo, Paolo; Sassi, Mauro; Beverina, Luca

doi:10.1002/ejoc.201500554

Cited by 9 publications

(12 citation statements)

References 34 publications

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“…Compound T3DPP-t-Boc was prepared by a slight modification of the protocol which we previously reported (see Figure S10 Supporting Information for the details). 33 PDI-t-Boc was prepared according to the reported procedure by Mattiello et al 43 Films preparation T3DPP-t-Boc and PDI-t-Boc were dissolved in chloroform (5 g/l) and deposited by spincoating at 1000 rpm for 60 s in air on low-alkali Corning 1737F glass. For the cleavage of the t-Boc group the films were annealed at 200 °C in air.…”

Section: Synthesis Of the Materialsmentioning

confidence: 99%

“…[40][41][42] Examples of a high electron affinity, t-Boc functionalized small molecule was only reported for a PDI-based latent pigment used in luminescent solar concentrators. 43 In this contribution, we report the use of thermo-cleavable t-Boc functionalized diketopyrrolopyrrole (DPP) and perylene-diimide (PDI) small molecules for the preparation of highly insoluble semiconducting layers in solution-processed top-gate FETs, thus enabling both p-and n-type staggered transistors and paving the way for the possible future use of this strategy in robust complementary circuits. The p-type FET is based on a terthiophene DPP molecule with t-Boc groups on the lactam N,N positions (T3DPP-t-Boc, Figure 1a), which has previously shown good potential for organic solar cells, but was not investigated for transistors applications.…”

Section: Introductionmentioning

confidence: 99%

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A latent pigment strategy for robust active layers in solution-processed, complementary organic field-effect transistors

et al. 2017

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Solution-processed organic semiconductors enable the fabrication of large-area and flexible electronics by means of cost-effective, solution-based mass manufacturing techniques.However, for many applications an insoluble active layer can offer technological advantages in terms of robustness to processing solvents. This is particularly relevant in field-effect transistors (FET), where processing of dielectrics or barriers from solution on top of the semiconductor layer typically imposes the use of orthogonal solvents in order not to interfere with the nanometer thick accumulation channel. To this end, the use of latent pigments, highly soluble molecules which can produce insoluble films after a post-deposition thermal cleavage of solubilizing groups, is a very promising strategy. In this contribution, we demonstrate the use of tert-Butyloxycarbonyl (t-Boc) functionalized diketopyrrolopyrrole and perylene-diimide small molecules for good hole and electron transporting films. t-Boc thermal cleavage produces a densification of the films, along with a strong structural rearrangement of the deprotected molecules, strongly improving charge mobility in both p-and n-type FET. We also highlight the robustness of these highly insoluble semiconducting layers to typical and aggressive processing solvents. These results can greatly enhance the degree of freedom in the manufacturing of multi-layered organic electronic devices, offering enhanced stability to harsh processing steps.

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Section: Synthesis Of the Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A latent pigment strategy for robust active layers in solution-processed, complementary organic field-effect transistors

et al. 2017

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“…[17][18][19][20] The advantage of such design lies in the complete removal of the insulating functionalizing chains from the active layer, often resulting in improvements of charge transport properties. [16,17,[21][22][23][24][25][26] Very recently, such an approach was extended to naphthalene diimide (NDI) containing polymers, one of the most promising classes of n-type polymeric semiconductors. [27,28] In this strategy, the imide nitrogen was functionalized -either directly or through an alkyl spacer -with a cleavable ester functionality.…”

Section: Introductionmentioning

confidence: 99%

“…The advantage of such design lies in the complete removal of the insulating functionalizing chains from the active layer, often resulting in improvements of charge transport properties …”

Section: Introductionmentioning

confidence: 99%

Preparation of Naphthalene Dianhydride Bithiophene Copolymers by Direct Arylation Polycondensation and the Latent Pigment Approach

et al. 2019

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An alternating naphthalene dianhydride bithiophene copolymer (PNDAT2) is prepared by a combined direct arylation polycondensation and the latent pigment approach. PNDAT2 is the first reported example of an alternating conjugated polymer containing naphthalene dianhydride, the oxo‐analogue of naphthalene diimide often used in electron‐acceptor conjugated polymers. PNDAT2 is resistant to organic solvents and can be generated directly as film by thermal treatment of the soluble tetraester precursor PNTET2. PNDAT2 is characterized by a LUMO level of −3.9 eV, similar to that of established naphthalene diimide containing soluble copolymers. This route to insoluble electron acceptor copolymers by thermal cleavage of soluble precursors is an alternative to classical cross‐linking or orthogonal processing strategies.

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“…Various different materials have been considered as fluorescent emitters for LSCs, such as colloidal quantum dots, metal‐organic complexes and organic dyes , . Among the latter, perylene‐based compounds have received special attention, thanks to the high efficiencies of the corresponding devices . In particular, Lumogen F Red 305 (LR, Figure ) is currently considered the state‐of‐the‐art for LSCs due to its very high fluorescence quantum yield and its excellent photostability , .…”

Section: Introductionmentioning

confidence: 99%

Green/Yellow‐Emitting Conjugated Heterocyclic Fluorophores for Luminescent Solar Concentrators

et al. 2018

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In this study, we report on the synthesis of new organic fluorophores containing either the benzo[1,2‐d:4,5‐d′]bisthiazole or the dithieno[3,2‐b:2′,3′‐d]silole heterocyclic unit, and on their application for the fabrication of luminescent solar concentrators (LSCs) made of poly(methyl methacrylate) (PMMA) thin films. In solution, the new compounds absorbed light in the visible region and displayed a brilliant green emission in the 500–600 nm range with moderate‐to‐good fluorescence quantum yields (0.25–0.68). Dispersions of selected fluorophores in PMMA thin films mostly maintained the light absorption features observed in solution, although in the case of benzobisthiazole‐based fluorophore 1a an evident fluorescence red‐shift was observed when increasing the compound concentration in the film. In agreement with its promising optical properties, LSCs prepared with the latter compound yielded interesting optical efficiencies up to 6.42 %, not far from those of state‐of‐the‐art PMMA LSC devices.

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First Demonstration of the Applicability of the Latent Pigment Approach to Plastic Luminescent Solar Concentrators

Cited by 9 publications

References 34 publications

A latent pigment strategy for robust active layers in solution-processed, complementary organic field-effect transistors

A latent pigment strategy for robust active layers in solution-processed, complementary organic field-effect transistors

Preparation of Naphthalene Dianhydride Bithiophene Copolymers by Direct Arylation Polycondensation and the Latent Pigment Approach

Green/Yellow‐Emitting Conjugated Heterocyclic Fluorophores for Luminescent Solar Concentrators

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