3,3'-Bis(octyloxy)-2,2'-bithiophene at 195 K

Pelletier, M; Brisse, F.; Cloutier, R.; Leclerc, Matthew C.

doi:10.1107/s0108270195001090

Cited by 10 publications

(13 citation statements)

References 4 publications

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“…The carbonitrile chain is almost linear, with the N1-C5-C2 bond angle being 177.43 (15)°. The geometric parameters are comparable with those observed in the related structures 3,3′-Bis(octyloxy)-2,2′-bithiophene at 195 K (Pelletier et al, 1995), 2,2′-(3,3′-Dihexyl-2,2′-bithiophene-5,5′-diyl) bis(4,4,5,5-tetramethyl-1,3,2-dioxa-borolane) [Huang & Li, 2011] and 3,3′-Didecyl-5,5,-bis(4-phenylquinolin-2-yl)-2,2′-bithienyl (Benedict et al, 2004).…”

Section: Data Collectionsupporting

confidence: 84%

“…For their applications, see: Deng et al (2011); Thomas et al (2008). For background to the title compound, see: Demanze et al (1996); Pletnev et al (2002); For related structures, see: Benedict et al (2004); Huang & Li (2011); Pelletier et al (1995); Li & Li (2009); Teh et al (2012). For thiophene C-S bond lengths, see: Howie & Wardell (2006).…”

Section: Related Literaturementioning

confidence: 99%

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2,2′-Bithiophene-3,3′-dicarbonitrile

Novina¹,

Vasuki²,

Karthik³

et al. 2012

Acta Cryst E

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The complete molecule of the title compound, C10H4N2S2, is generated by an inversion center situated at the mid-point of the bridging C—C bond. The bithiophene ring system is planar [maximum deviation = 0.003 (2) Å] and the central C—C bond length is 1.450 (2) Å. There are no significant intermolecular interactions in the crystal structure, which is stabilized by van der Waals interactions.

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Section: Data Collectionsupporting

confidence: 84%

Section: Related Literaturementioning

confidence: 99%

2,2′-Bithiophene-3,3′-dicarbonitrile

Novina¹,

Vasuki²,

Karthik³

et al. 2012

Acta Cryst E

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“…For the S 0 geometries, the dihedral angle between A and D1 gradually enlarges with the increase of side-chain steric hindrance on D1: 2° for IR-FTT , 42° for IR-FTE , 45° for IR-FTG , and 58° for IR-FTA . IR-FTE exhibits a small dihedral angle between D1 and D2 due to the oxygen (EDOT)–sulfur (D2 thiophene) interaction. − The dihedral angles between D2 and fluorene shielding unit (S) in the IR-FTX fluorophores are similar with values of 30°–33°. By adding up all the three dihedral angles (A–D1, D1–D2, and D2–S), it yields the twist between shielding unit and acceptor, which follows the order: IR-FTA > IR-FTG > IR-FTE > IR-FTT .…”

Section: Resultsmentioning

confidence: 90%

Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance

et al. 2018

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Organic fluorophores have been widely used for biological imaging in the visible and the first near-infrared windows. However, their application in the second near-infrared window (NIR-II, 1000-1700 nm) is still limited mainly due to low fluorescence quantum yields (QYs). Here, we explore molecular engineering on the donor unit to develop high performance NIR-II fluorophores. The fluorophores are constructed by a shielding unit-donor(s)-acceptor-donor(s)-shielding unit structure. Thiophene is introduced as the second donor connected to the shielding unit, which can increase the conjugation length and red-shift the fluorescence emission. Alkyl thiophene is employed as the first donor connected to the acceptor unit. The bulky and hydrophobic alkyl thiophene donor affords larger distortion of the conjugated backbone and fewer interactions with water molecules compared to other donor units studied before. The molecular fluorophore IR-FTAP with octyl thiophene as the first donor and thiophene as the second donor exhibits fluorescence emission peaked at 1048 nm with a QY of 5.3% in aqueous solutions, one of the highest for molecular NIR-II fluorophore reported so far. Superior temporal and spatial resolutions have been demonstrated with IR-FTAP fluorophore for NIR-II imaging of the blood vessels of a mouse hindlimb.

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“…The uncomplexed polythiophene is highly planar, while metal complexation with the crown ether results in twisted polymer backbone in order to accommodate maximum chelation, which shows selective ionochromic response . The backbone coplanarity in the uncomplexed head-to-head linkage containing polythiophene is due to the reduced steric hindrance using alkoxy chain versus alkyl chain and the intramolecular noncovalent (thienyl)S···(alkoxy)O interaction, − which is indeed the basis for the design of the widely used conducting polymer PEDOT. − Inspired by the great success of alkoxy-substituted thiophene in semiconducting and conducting polymers, we designed and synthesized a novel electron donor unit, 3,3′-dialkoxy-2,2′-bithiophene (BTOR, Figure a), to address the issue of reduced solubility and maintaining backbone coplanarity of polymer for organic electronics. , The intramolecular noncovalent S···O interaction can lock conformation and promote backbone coplanarity in the head-to-head linkage containing bithiophene. − By inserting oxygen atom into 3,3′-dialkyl-2,2′-bithiophene, a novel electron donor unit, 3,3′-dialkoxy-2,2′-bithiphene (BTOR, Figure a), was designed and synthesized successfully. Two solubilizing alkoxy chains on the 3,3′-positions of bithiophene afford polymers with excellent solubility, and the conformation locking via intramolecular noncovalent S···O interaction leads to polymers with high degree of backbone coplanarity, narrow bandgap, and substantial crystallinity.…”

Section: Introductionmentioning

confidence: 99%

Head-to-Head Linkage Containing Dialkoxybithiophene-Based Polymeric Semiconductors for Polymer Solar Cells with Large Open-Circuit Voltages

et al. 2016

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High degree of polymer backbone planarity is achieved by incorporating intramolecular noncovalent sulfur••• oxygen interaction, which also affords good solubility by attaching alkoxy chains at the 3,3′-positions of bithiophene. However, the applications of the resulting polymers are plagued by their highlying HOMOs due to the strong electron-donating alkoxy chains, resulting in small open-circuit voltages (V oc s) in polymer solar cells. Herein, a novel head-to-head linkage containing 3,3′dialkoxy-4,4′-dicyano-2,2′-bithiophene (BTCNOR) is invented. Single-crystal X-ray diffraction shows direct evidence of noncovalent sulfur•••oxygen interaction and coplanar backbone of BTCNOR. Very low-lying HOMOs (−5.5 to −5.6 eV) of the corresponding polymers with high degree of backbone planarity and good solubility are achieved by introducing strong electronwithdrawing cyano group onto the dialkoxybithiophene. The cyano offsets the effect of the electron-donating alkoxy chain, rendering the new BTCNOR as a weak donor unit. With this approach, polymer solar cells fabricated from BTCNOR-based polymers deliver very large V oc s (0.9−1.0 V). By varying the BTCNOR side chains, the highest power conversion efficiency of 7.13% is obtained. Diverse characterization techniques are performed to elucidate the structure−property correlations of the new BTCNOR-based semiconductors. The results demonstrate that incorporating strong electron-withdrawing groups into the highly electron-rich dialkoxybithiophene can lead to improved optoelectrical property. The study offers a promising materials design strategy for high-performance organic electronics.

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3,3'-Bis(octyloxy)-2,2'-bithiophene at 195 K

Cited by 10 publications

References 4 publications

2,2′-Bithiophene-3,3′-dicarbonitrile

2,2′-Bithiophene-3,3′-dicarbonitrile

Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance

Head-to-Head Linkage Containing Dialkoxybithiophene-Based Polymeric Semiconductors for Polymer Solar Cells with Large Open-Circuit Voltages

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