Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• phenyl-C61-butyric acid methyl ester (PCBM) acceptor when used in bulk heterojunction polymer solar cell devices with poly(3-hexylthiophene) (P3HT) as the donor material. This improvement was attributed to the anchoring effect of the bulkier groups present in TQT-C60, which hindered the movement and

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• promising. They are synthesized in two main reactions: nucleophilic cyclopropanation according to the Bingel method and thermal addition of diazo compounds. This present review summarizes the material on the synthesis of monofunctionalized methanofullerenes – analogues of [60]PCBM – based on various diazo

• ]PCBM; diazo compounds; mechanisms and optimal conditions of cyclopropanation; methanofullerenes C60; Introduction Taking into consideration that all life on Earth is of organic origin. with carbon as its basic element (20% by weight of every living organism, and the fourth most abundant element in the

• structure. Of the series of monophenylmethanofullerenes, the practically important so-called [6,6]-phenyl-C61-butyric acid methyl ester [60]PCBM synthesized by Hummelen, Wudl, and co-workers is most prominent (Scheme 13) [96]. The authors modified [60]PCBM via acid chloride 43 to give derivatives of

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• fullerene 20b because the strong electron-withdrawing property of fluorine reverses the relationship between the electronic states of both units [105]. It was suggested that TFEO-Pc has an orbital energy closer to that of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) [106][107], which is a known

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• , EHOMO, DFT: −4.97 eV). We anticipate this should provide a high VOC when blended with PCBM. The band gap of p-SIDT(FBTThCA8)2 is also reduced with respect to p-SIDT(FBTTh2)2 as determined by CV (1.72 eV and 1.85 eV, respectively) and by DFT (1.90 eV and 2.01 eV, respectively) suggesting that

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• ester (PCBM, Figure 1d). Decreasing the energy levels of the parent Zn(WS3)2 would enable this new class of acceptors to be paired with other polymer donors that have lower HOMO and LUMO energy levels than P3HT. One substituent used to modify the properties of molecules without drastically altering the

• and L3 chelates. The estimated HOMO and LUMO energy levels obtained from cyclic voltammetry are shown in Figure 8. The HOMO and LUMO of Zn(L1)2 and Zn(L4)2 approach those of PCBM. Crystallography Single crystals of the zinc(II) chelates were grown in order to better understand the structure of the

• the absorption spectra, both in solution and film. Preliminary results in OPVs suggest that fluorination is generally beneficial for device performance of zinc(II) azadipyrromethene-based acceptors. In particular, Zn(L4)2 is the best candidate to directly replace PCBM due to similar energy levels and

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• commonly phenyl-C61-butyric acid methyl ester (PCBM), as the electron acceptor [4][5][6][7][8][9]. However, there is growing interest in the use of small molecules as donor materials in OPVs [10][11][12][13][14][15][16][17]. This interest derives from advantages and properties that small molecules show

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• conversion efficiencies of about 2% were measured in the P3HT/AIM devices with 1:0.4 P3HT:AIM weight ratio for the AIMs with hexadecyl and dodecyl substituents. From the optical and AFM data, we suggested that the AIMs, in contrast to [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), do not disturb the P3HT

• popular fullerene derivative in organic photovotaics is (PCBM) [4][5][6]. As an alternative to PCBM, we recently suggested indolinone-substituted methanofullerenes (IM) [7]. The principal advantages of IM are their easier synthesis and purification as compared to PCBM [7][8]. Indeed, the IM can be

• suggested that the coarser surface morphology in the P3HT/HBIM blends is a result of the fullerene-rich domains, which are too large for the optimal polymer–fullerene phase separation. Possibly, the coarser surface morphology is due to the lower solubility of HBIM as compared to PCBM. Usually, alkyl

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

• Rohan J. Kumar,
• Jegadesan Subbiah and
• Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

• organic photovoltaic devices fabricated with 1:1 blends of 2 with PCBM it was observed that the fill factor increased in comparison with the data reported for a similar molecule (1) that did not show evidence of self-organization. The use of designed hydrogen-bonding interactions to produce hierarchical

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• electron-rich quaterthiophene derivative with the electron acceptor [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) revealed a nanoscale segregated assembly of the individual building blocks in the blend. Keywords: charge transport; hydrogen bonding; oligothiophene; organogel; self-assembly

• studies of trialkoxybenzamide-functionalized quaterthiophene derivative T1 (Scheme 1). We also present our initial results on the morphology of blends of this electron-rich p-type semiconducting T1 with the well-known n-type semiconductor [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). Results and

• concentration of 5 x 10−5 M. Studies on blends of T1 with PCBM The fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) is a well-known n-type semiconductor and its blends with various electron-donor materials have been extensively used in solar cell devices [24]. The morphology of the blend

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• polymer such as P-15 (Table 2) exhibited absorption and fluorescence maxima of 510 and 585 nm, respectively, the fluorescence quantum yield being 66%. Polymer/PCBM bulk heterojunction solar cells exhibited a power conversion efficiency of 0.16%. Cao et al. [53] prepared new fluorene-DPP-phenothiazine

Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices

• Yves Henri Geerts,
• Olivier Debever,
• Claire Amato and
• Sergey Sergeyev

Beilstein J. Org. Chem. 2009, 5, No. 49, doi:10.3762/bjoc.5.49

• , firstly in the pristine form and later as easily soluble derivatives such as phenylcyclopropa[6,6]C60-butanoic acid methyl ester (PCBM, 1, Figure 1) [9][10][11][12]. It has been used in a combination with a plethora of conjugated polymers [13][14][15][16][17][18] as well as small molecules [19][20][21

• Discussion The structure of dyads 2a–d is depicted in Figure 1. We decided to combine in one molecule the phenylcyclopropa[6,6]C60 moiety of PCBM as an acceptor and a phthalocyanine bearing three swallow-tail alkoxy groups as a donor. The choice of the substituents on the phthalocyanine core was dictated by

• phthalocyanine derivatives: they feature two intense long-wave absorption bands (termed Q-bands). In the final synthetic step, reaction between 4a–d and the acid 11 (prepared by acid-catalyzed hydrolysis of the commercially available methyl ester 1, PCBM) [10][58] afforded the corresponding dyads 2a–d (Scheme 2

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• solvents, an important property in processing cells. First reduction potentials of most derivatives were less negative than that of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), which is possibly ascribed to their electron-withdrawing nature. Organic thin-film photovoltaic cells fabricated with poly(3

• -hexylthiophene) (P3HT) as the electron-donor and diarylmethanofullerene derivatives as the electron-acceptor material were examined. The {(methoxycarbonyl)phenyl[bis(octyloxy)phenyl]methano}fullerene showed power conversion efficiency as high as PCBM, but had higher solubility in a variety of organic solvents

• than PCBM. The Voc value was higher than that of PCBM, which is derived from the electron-donating (octyloxy)phenyl group, possibly raising the LUMO level. Photovoltaic effects of the devices fabricated with the derivatives having some electron-withdrawing groups were also examined. Keywords: bulk

Synthesis of thienyl analogues of PCBM and investigation of morphology of mixtures in P3HT

• Fukashi Matsumoto,
• Kazuyuki Moriwaki,
• Yuko Takao and
• Toshinobu Ohno

Beilstein J. Org. Chem. 2008, 4, No. 33, doi:10.3762/bjoc.4.33

• Fukashi Matsumoto Kazuyuki Moriwaki Yuko Takao Toshinobu Ohno Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan. 10.3762/bjoc.4.33 Abstract Novel [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) analogues containing benzo[b]thiophene (3a, 3b) and

• methanofullerenes was performed by using dichloromethane as a solvent. es-TThCBM (3d) exhibited 1.4 times greater solubility in dichloromethane than PCBM. Keywords: fullerene; morphology; organic fullerenes; PCBM; photovoltaic cell; Introduction The demand for inexpensive, renewable energy sources continues to

• , Figure 1) with [6,6]-phenyl-C61-butyric acid methyl ester (PCBM, Figure 1) are highly efficient and promising devices [10]. Many efforts have been devoted to improve device efficiency, for example, changing the solvent for the spin coating of the active layer [11][12], annealing the device to improve the