Small Molecular Aryl Acetylenes: Chemically Tailoring High‐Efficiency Organic Semiconductors for Solar Cells and Field‐Effect Transistors

Broggi, Alessandra; Tomasi, Ivan; Bianchi, Luca; Marrocchi, Assunta; Vaccaro, Luigi

doi:10.1002/cplu.201400001

Cited by 47 publications

(21 citation statements)

References 191 publications

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“…6 (ii) Alkynyl substituents on polycyclic aromatic rings often impart interesting or valuable excited state emission properties. 7 Accordingly, one of the early reactions we explored was that between the tetrayne 9a and TPCP ( 3 , Figure 2). 8 The symmetry of this HDDA substrate make it attractive from a preparative perspective.…”

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confidence: 99%

Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels–Alder Cascade Reaction

Hershey

Holmes

et al. 2016

J. Am. Chem. Soc.

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We describe here three alkynyl substituted naphthalenes that display promising luminescence characteristics. Each compound is easily and efficiently synthesized in three steps by capitalizing on the hexadehydro-Diels–Alder (HDDA) cycloisomerization reaction in which an intermediate benzyne is captured by tetraphenylcyclopentadienone, a classical trap for benzyne itself. These compounds luminesce in the deep blue when stimulated either optically (i.e., photoluminescence in both solution and solid films) or electrically [in a light-emitting diode (LED)]. The photophysical properties are relatively insensitive to the electronic nature of the substituents (H, OMe, CO2Me) that define these otherwise identical compounds. Overall, our observations suggest that the twisted nature of the five adjacent aryl groups serves to minimize the intermolecular interaction between core naphthalene units in different sample morphologies. These compounds represent promising leads for the identification of others of value as the emissive component of organic LEDs (OLEDs).

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confidence: 99%

Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels–Alder Cascade Reaction

Hershey

Holmes

et al. 2016

J. Am. Chem. Soc.

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“…Conversely, solution-processed conjugated small molecules have attracted significant attention as candidates for active materials in BHJ solar cells as p-type semiconductor components due to their well-defined molecular structures and molecular weights and their easy purification methods [25][26][27][28][29][30]. Thus, various types of small molecules such as organic dyes, [31][32][33][34][35] oligothiophenes, [36][37][38][39][40] and D-A type molecules have been designed and synthesized to optimize the BHJ solar cell systems [41][42][43][44][45].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthetic Route of a Solution-Processable, Thieno[3,4-c]pyrrolo-4,6-dione-Based Conjugated Small Molecule and Control of the Optoelectronic Properties via Processing Additives

Kwon¹,

Lim

Park

et al. 2018

Applied Sciences

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In this study, a new type of low-bandgap small molecule has been synthesized with a thieno[3,4-c]pyrrole-4,6-dione (TPD) derivative for application in bulk heterojunction (BJH) solar cells. The series of solar cells were fabricated by blending the TPD-based small molecule (M1) and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM). In order to optimize the performance of solar cells, the nanoscale morphologies of the BHJ layers were controlled via processing additives with 1,8-diiodooctane (DIO) and 1-chloronaphthalene (CN). Therefore, we demonstrated that the use of CN successively suppressed molecular aggregation and demonstrated suitable phase separation, in addition to increasing the power conversion efficiency from 0.36% to 1.86%.

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“…Finally, various ethynylated derivatives 6 have been described by us recently [ 15 ], compounds that, inter alia, are of interest in materials science [ 16 – 18 ].…”

Section: Introductionmentioning

confidence: 99%

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

Hopf¹,

Narayanan²,

Jones³

2015

Beilstein J. Org. Chem.

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SummaryThe two isomeric bis(isocyanates) 4,12- and 4,16-di-isocyanato[2.2]paracyclophane, 16 and 28, have been prepared from their corresponding diacids by simple routes. The two isomers are versatile intermediates for the preparation of various cyclophanes bearing substituents with nitrogen-containing functional groups, e.g., the pseudo-ortho diamine 8, the bis secondary amine 23, and the crownophanes 18 and 19. Several of these new cyclophane derivatives (18, 19, 22, 26, 28) have been characterized by X-ray structural analysis.

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Small Molecular Aryl Acetylenes: Chemically Tailoring High‐Efficiency Organic Semiconductors for Solar Cells and Field‐Effect Transistors

Cited by 47 publications

References 191 publications

Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels–Alder Cascade Reaction

Blue-Emitting Arylalkynyl Naphthalene Derivatives via a Hexadehydro-Diels–Alder Cascade Reaction

Facile Synthetic Route of a Solution-Processable, Thieno[3,4-c]pyrrolo-4,6-dione-Based Conjugated Small Molecule and Control of the Optoelectronic Properties via Processing Additives

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

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