Synthesis and characterization of new electron donors containing 1,2,5-thiadiazole and 1,1′-dihydro-4,4′-bi(pyridylidene) units

Yamashita, Yoshiro; Ono, Katsuhiko; Tomura, Masaaki; Imaeda, Kenichi

doi:10.1039/a704375i

Cited by 22 publications

(8 citation statements)

References 9 publications

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“…Preparation 4,4 0 -Dimethyl-7,7 0 -bi( [1,2,5]thiadiazolo [3,4-b]pyridylidene) was synthesized according to the literature method [9]. Chloranilic acid was purchased from Tokyo Chemical Industry Co. Ltd.…”

Section: Methodsmentioning

confidence: 99%

“…If we consider intermolecular heteroatom interactions as connection tools, various types of heterocycles can be applied to molecular building blocks. We have synthesized unique molecules containing two fused 1,2,5-thiadiazole rings, benzobis(thiadiazole) [8] and bi(thiadiazolopyridylidene) [9] derivatives, so far. One-dimensional supramolecular tape structures linked by short intermolecular SÁÁÁN heteroatom interactions at the 1,2,5-thiadiazole rings were observed in their crystalline state.…”

Section: Introductionmentioning

confidence: 99%

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Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

2008

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The molecular and crystal structure of a 1:1 co-crystal of 4,4 0 -dimethyl-7,7 0 -bi ([1,2,5]thiadiazolo [3,4-b] pyridylidene)-chloranilic acid, (1), has been determined by X-ray diffraction at the monoclinic space group P2 1 /c with cell parameters of a = 8.422(6), b = 7.343(4), c = 16.112(7) Å , b = 104.988(8)°, V = 962.5(10) Å 3 and Z = 2. In the crystal structure, two components connect via the intermolecular O-HÁÁÁN hydrogen bonds [2.804(4) Å ] and SÁÁÁO heteroatom interaction [2.945(3) Å ] with R 2 2 (7) couplings to form a unique and infinite one-dimensional supramolecular tape structure. The calculations of (1) at the HF/6-31G(d), MP2/6-31G(d), and B3LYP/6-31G(d) levels can almost reproduce X-ray geometry. In addition, the distances of the intermolecular O-HÁÁÁN and SÁÁÁO interactions by MP2/6-31G(d) and B3LYP/6-31G(d) levels agree well with those in the crystal. The calculated binding energies corrected BSSE and ZPE are -4.487 (HF), -7.473 (MP2), and -5.640 (B3LYP) kcal/mol. The results suggest that the complex (1) is very stable and the dispersion interaction is significantly important for the attractive intermolecular interaction in (1). The NBO analysis has revealed that the n(N) ? r*(O-H) interaction gives the strongest stabilization to the system and the major interaction for the intermolecular SÁÁÁO contact is n(O) ? r*(S-N).

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

2008

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“…The angle between the dimers is 111 (1)°. This type of a unique multi-dimensional structure is important for the construction of organic conducting materials (Barclay et al, 2000;Kato et al, 1988;Morimoto & Inabe, 1995;Tomura & Yamashita, 2000;Yamashita et al, 1997Yamashita et al, , 1998.…”

Section: Figurementioning

confidence: 99%

Tetrathiafulvalene with a fused pyrazine ring

Tomura

Yamashita

2001

Acta Cryst E

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“…The benzothiadiazole group acts both as an electron transporting and highly fluorescent chromophore. Interestingly, the coupling of benzothiadiazole with thiophene units represent a useful material combination, which provides red-shifted UV–vis and emission spectra compared to equivalent oligothiophenes, ,− essentially required in order to harvest low energy (viz. near-infrared and visible) photons.…”

Section: Introductionmentioning

confidence: 99%

Strategical Designing of Donor–Acceptor–Donor Based Organic Molecules for Tuning Their Linear Optical Properties

2018

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Low-energy linear absorption spectrum of a series of 48 donor-acceptor-donor (D-A-D) scheme based thiophone-benzo(bis-)X-diazole molecules with X = O, S, Se, or Te are calculated using time dependent density functional theory in order to propose strategical design of molecules that can efficiently absorb light in the infrared and visible region of the solar spectrum. Our study establishes that optical properties of the D-A-D based organic molecules significantly depend on the donor-to-acceptor (D/A) ratio and the strength of the acceptor moiety. Thus, by choice of a suitable D/A ratio and type of the acceptor moiety, the linear absorption spectrum can be largely shifted, in general, while the optical gap can be engineered over a wide energy range of ∼0.2-2.3 eV, in particular. It is also noticed that the increase in acceptor units (i.e., when D/A ≤ 1) leads to increase in steric hindrance in between them. This, in turn, disrupts the effective conjugation length and increases the optical gap. However, this effect is found to dominate strongly in the bis-configurations of the molecules as compared to the nonbis compositions. In order to reduce this effect for rational designing of effective D-A-D type chromophores with less steric hindrance, the role of π-conjugated ethylene (-CH═CH-) linkage/spacer between the A-A units is explored further. Here, it is found that introduction of such linkage substantially decreases the steric hindrance and, thereby, the optical gap as well. Besides this, our study also highlights and explains the impact of the acceptor moiety in improving the absorption capabilities of these molecules in the low-energy region.

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Synthesis and characterization of new electron donors containing 1,2,5-thiadiazole and 1,1′-dihydro-4,4′-bi(pyridylidene) units

Cited by 22 publications

References 9 publications

Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

Tetrathiafulvalene with a fused pyrazine ring

Strategical Designing of Donor–Acceptor–Donor Based Organic Molecules for Tuning Their Linear Optical Properties

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