Photocyclization of terthiophenes

Jayasuriya, Nimal; Kagan, Jacques; Owens, J. E.; Kornak, Eugene P.; Perrine, D.

doi:10.1021/jo00278a039

Cited by 42 publications

(25 citation statements)

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“…We only briefly mention here the possibility of ring closure of the terthiophene unit. Benzo[1,2‐b:3,4‐b′:6,5‐b″]trithiophene was obtained by photocyclisation under harsh conditions using UV‐light at 320–400 nm and catalytic amounts of iodine . This photocyclisation becomes reversible at room temperature without the need for catalytic iodine using 3T‐derivative 6.…”

Section: Structurally Well‐defined Branched Thiophenes: From Small Momentioning

confidence: 99%

“…Benzo[1,2-b:3,4-b′:6,5-b″] trithiophene was obtained by photocyclisation under harsh conditions using UV-light at 320-400 nm and catalytic amounts of iodine. [ 26 ] This photocyclisation becomes reversible at room temperature without the need for catalytic iodine using 3T-derivative 6. [ 27 ] The signifi cant difference between the absorption of the open ( 6 , λ(Abs) max = 254 nm) and the closed form (λ(Abs) max = 465 nm) makes it a potential material for rewritable photochromic devices.…”

Section: T-terthiophene As Building Blockmentioning

confidence: 99%

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Branched Terthiophenes in Organic Electronics: From Small Molecules to Polymers

Scheuble

Goll

Ludwigs

2014

Macromol. Rapid Commun.

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A zoo of chemical structures is accessible when the branched unit 2,2':3',2″-terthiophene (3T) is included both in structurally well-defined small molecules and polymer-like architectures. The first part of this review article highlights literature on all-thiophene based branched oligomers including dendrimers as well as combinations of 3T-units with functional moieties for light-harvesting systems. Motivated by the perfectly branched macromolecular dendrimers both electropolymerization as well as chemical approaches are presented as methods for the preparation of branched polythiophenes with different branching densities. Structure-function relationships between the molecular architecture and optical and electronic properties are discussed throughout the article.

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Section: Structurally Well‐defined Branched Thiophenes: From Small Momentioning

confidence: 99%

Section: T-terthiophene As Building Blockmentioning

confidence: 99%

Branched Terthiophenes in Organic Electronics: From Small Molecules to Polymers

Scheuble

Goll

Ludwigs

2014

Macromol. Rapid Commun.

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“…In the presence of a catalytic amount of iodine, polycyclic hydrocarbon 2 was readily prepared in 55% yield via oxidative photocyclization by the UV irradiation of a diluted toluene solution of compound 1 under ambient conditions. [21][22][23] Two a protons of the precursor monomer 2 were then quantitatively removed via applying BuLi. The deprotonated intermediate was subsequently quenched in situ by either trimethyltin chloride or iodine to afford the distannyl monomer 3 or the diiodinated monomer 4, respectively.…”

Section: Synthesis and Characterization Of Monomers And Polymersmentioning

confidence: 99%

Conjugated Polymer Based on Polycyclic Aromatics for Bulk Heterojunction Organic Solar Cells: A Case Study of Quadrathienonaphthalene Polymers with 2% Efficiency

Xiao

Stuart

Liu

et al. 2010

Adv Funct Materials

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Polycyclic aromatics offer great flexibility in tuning the energy levels and bandgaps of resulting conjugated polymers. These features have been exploited in the recent examples of benzo[2,1‐b:3,4‐b']dithiophene (BDT)‐based polymers for bulk heterojunction (BHJ) photovoltaics (ACS Appl. Mater. Interfaces 2009, 1, 1613). Taking one step further, a simple oxidative photocyclization is used here to convert the BDT with two pendent thiophene units into an enlarged planar polycyclic aromatic ring—quadrathienonaphthalene (QTN). The reduced steric hindrance and more planar structure promotes the intermolecular interaction of QTN‐based polymers, leading to increased hole mobility in related polymers. As‐synthesized homopolymer (HMPQTN) and donor–acceptor polymer (PQTN‐BT) maintain a low highest occupied molecular orbital (HOMO) energy level, ascribable to the polycyclic aromatic (QTN) moiety, which leads to a good open‐circuit voltage in BHJ devices of these polymers blended with PCBM ([6,6]‐phenyl‐C61‐butyric acid methyl ester; HMPQTN: 0.76 V, PQTN‐BT: 0.72 V). The donor–acceptor polymer (PQTN‐BT) has a smaller optical bandgap (1.6 eV) than that of HMPQTN (2.0 eV), which explains its current (5.69 mA cm−2) being slightly higher than that of HMPQTN (5.02 mA cm−2). Overall efficiencies over 2% are achieved for BHJ devices fabricated from either polymer with PCBM as the acceptor.

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“…TDDFT calculations for both BTT3 and BTT4 show almost similar absorption maxima at 362 and 359 nm, respectively and also the transitions from HOMO to LUMO. In the case of unsymmetrical BTTs, the experimentally reported absorption for BTT5 was at 335 nm and the TDDFT‐calculated value was 314 nm . The major transitions in BTT5 were from HOMO − 1 to LUMO, HOMO to LUMO, and HOMO to LUMO + 1.…”

Section: Resultsmentioning

confidence: 99%

“…Later on, an efficient method for preparation of symmetrical BTT (BTT1; Scheme ) with its electronic excitations similar to triphenylene and with the absorption maximum at 320 nm was reported by Hart and Sasaoka in 1978 . Next, symmetrical and unsymmetrical BTT (BTT2 and BTT5 in Scheme ) were successfully prepared by Jayasuriya and Kagan in 1989 . Roncali et al demonstrated the remarkable applications of star‐shaped, fused oligothiophene‐based BTT‐core compounds in photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

Optoelectronic properties of benzotrithiophene isomers: A density functional theory study

Tripathi

2019

J Chinese Chemical Soc

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Benzotrithiophene (BTT) isomers were investigated using density functional theory (DFT) and time‐dependent DFT (TD‐DFT) with the aim to explore their structures, linear optical properties, vertical and adiabatic ionization potentials (IPv and IPa), electron affinities (EAv and EAa), and reorganization energies (λ). The computed bond lengths and bond angles at the B3LYP/6–311+G (d, p) level of theory are in good agreement with experimental crystal structures of the known BTTs. These molecules are planar with zero dihedral angle, making them an ideal backbone for high charge mobility. The UV–visible spectra of BTT isomers are in the range 280–360 nm. All BTT isomers have low hole/electron reorganization energies, which is the main characteristic of good hole/electron transporting materials, and these isomers in turn have potential applications in the field of organic materials.

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Photocyclization of terthiophenes

Cited by 42 publications

References 0 publications

Branched Terthiophenes in Organic Electronics: From Small Molecules to Polymers

Branched Terthiophenes in Organic Electronics: From Small Molecules to Polymers

Conjugated Polymer Based on Polycyclic Aromatics for Bulk Heterojunction Organic Solar Cells: A Case Study of Quadrathienonaphthalene Polymers with 2% Efficiency

Optoelectronic properties of benzotrithiophene isomers: A density functional theory study

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