Efficient Spontaneous and Stimulated Emission from 1,4‐Bis(2,2‐diphenylvinyl)benzene Single Crystals with Cross‐Dipole Stacking
Abstract
Organic single crystals with cross-dipole stacking based on 1,4-bis(2,2-diphenylvinyl)benzene are prepared. X-ray diffraction shows that adjacent molecules in the single crystal adopt a rotational angle of ≈62°. Such a stacking mode is highly beneficial for spontaneous and stimulated emission, resulting in high solid-state fluorescence efficiency and excellent amplified spontaneous emission characteristics.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Molecules possessing predominant X-type stacking are still quite rare, mainly due to the difficulty of molecular design and structural modification requirements.
“While cross-dipole stacking has been addressed as a preferred motif for aggregated state emission, molecules possessing predominant X-type stacking are still quite rare. This is mainly due to the difficulty of the molecular design and structural modification requirements.93−96”
Cites
The nature of .pi.-.pi. interactions
Hunter, C. A., & Sanders, J. K. M. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00170a016 · Cited by 5,365 · see citing works
The exciton model in molecular spectroscopy
Kasha, M., Rawls, H. R., & Ashraf El-Bayoumi, M. (1965) · Pure and Applied Chemistry · doi:10.1351/pac196511030371 · Cited by 4,253 · see citing works
Wang, C., Dong, H., Hu, W., Liu, Y., & Zhu, D. (2011) · Chemical Reviews · doi:10.1021/cr100380z · Cited by 3,610 · see citing works
Samuel, I. D. W., & Turnbull, G. A. (2007) · Chemical Reviews · doi:10.1021/cr050152i · Cited by 1,466 · see citing works
Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors
Mei, J., Diao, Y., Appleton, A. L., Fang, L., & Bao, Z. (2013) · Journal of the American Chemical Society · doi:10.1021/ja400881n · Cited by 1,443 · see citing works
Yoon, S.-J., Chung, J. W., Gierschner, J., Kim, K. S., Choi, M., Kim, D., & Park, S. Y. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1044665 · Cited by 949 · see citing works
Effect of impurities on the mobility of single crystal pentacene
Jurchescu, O. D., Baas, J., & Palstra, T. T. M. (2004) · Applied Physics Letters · doi:10.1063/1.1704874 · Cited by 857 · see citing works
An, B.-K., Gierschner, J., & Park, S. Y. (2012) · Accounts of Chemical Research · doi:10.1021/ar2001952 · Cited by 743 · see citing works
Spectral Engineering in π-Conjugated Polymers with Intramolecular Donor−Acceptor Interactions
Beaujuge, P. M., Amb, C. M., & Reynolds, J. R. (2010) · Accounts of Chemical Research · doi:10.1021/ar100043u · Cited by 617 · see citing works
Cornil, J., dos Santos, D. A., Xavier Crispin, A., Silbey, R., & Brédas, J. (1998) · Journal of the American Chemical Society · doi:10.1021/ja973761j · Cited by 601 · see citing works
Laser action in organic semiconductor waveguide and double-heterostructure devices
Kozlov, V. G., Bulović, V., Burrows, P. E., & Forrest, S. R. (1997) · Nature · doi:10.1038/38693 · Cited by 489 · see citing works
Xie, Z., Yang, B., Li, F., Cheng, G., Liu, L., Yang, G., Xu, H., Ye, L., Hanif, M., Liu, S., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054661d · Cited by 382 · see citing works
Park, S., Kwon, O., Kim, S., Park, S., Choi, M., Cha, M., Park, S. Y., & Jang, D. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0508727 · Cited by 348 · see citing works
Amplified spontaneous emission from photopumped films of a conjugated polymer
McGehee, M. D., Gupta, R., Veenstra, S., Miller, E. K., Díaz‐García, M. A., & Heeger, A. J. (1998) · Physical review. B, Condensed matter · doi:10.1103/physrevb.58.7035 · Cited by 320 · see citing works
Wang, K., Zhang, H., Chen, S., Yang, G., Zhang, J., Tian, W., Su, Z., & Wang, Y. (2014) · Advanced Materials · doi:10.1002/adma.201401114 · Cited by 309 · see citing works
Self-citationHigh Mobility and Luminescent Efficiency in Organic Single‐Crystal Light‐Emitting Transistors
Bisri, S. Z., Takenobu, T., Yomogida, Y., Shimotani, H., Yamao, T., Hotta, S., & Iwasa, Y. (2009) · Advanced Functional Materials · doi:10.1002/adfm.200900028 · Cited by 261 · see citing works
Controlling the Structures and Photonic Properties of Organic Nanomaterials by Molecular Design
Yao, W. F., Yan, Y., Lin, X., Zhang, C., Li, G., Zheng, Q., Zhao, Y. S., Jiang, H., & Yao, J. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201302894 · Cited by 214 · see citing works
Material marriage in electronics
Meijer, E. W., & Schenning, A. P. H. J. (2002) · Nature · doi:10.1038/419353a · Cited by 180 · see citing works
An Organic Luminescent Molecule: What Will Happen When the “Butterflies” Come Together?
Zhang, J., Xu, B., Chen, J., Ma, S., Dong, Y., Wang, L., Li, B., Ye, L., & Tian, W. (2013) · Advanced Materials · doi:10.1002/adma.201303639 · Cited by 166 · see citing works
Self-citationImproved Crystal‐Growth and Emission Gain‐Narrowing of Thiophene/Phenylene Co‐Oligomers
Ichikawa, M., Hibino, R., INOUE, M., Haritani, T., Hotta, S., Koyama, T., & Taniguchi, Y. (2003) · Advanced Materials · doi:10.1002/adma.200390048 · Cited by 159 · see citing works
Light amplification and gain in polyfluorene waveguides
Heliotis, G., Bradley, D. D. C., Turnbull, G. A., & Samuel, I. D. W. (2002) · Applied Physics Letters · doi:10.1063/1.1494473 · Cited by 153 · see citing works
Yang, C., Cho, A. T., Pan, F., Tsai, T. G., & Chao, K. J. (2001) · Advanced Materials · doi:10.1002/1521-4095(200107)13:14 · Cited by 147 · see citing works
Ichikawa, M., Nakamura, K., Inoue, M., Mishima, H., Haritani, T., Hibino, R., Koyama, T., & Taniguchi, Y. (2005) · Applied Physics Letters · doi:10.1063/1.2138361 · Cited by 122 · see citing works
Cyano‐Substituted Oligo(p‐phenylene vinylene) Single Crystals: A Promising Laser Material
Wang, H., Li, F., Ravia, I., Gao, B., Li, Y., Medvedev, V., Sun, H., Tessler, N., & Ma, Y. (2011) · Advanced Functional Materials · doi:10.1002/adfm.201100783 · Cited by 107 · see citing works
Low‐Threshold Nanolasers Based on Slab‐Nanocrystals of H‐Aggregated Organic Semiconductors
Xu, Z., Liao, Q., Shi, Q., Zhang, H., Yao, J., & Fu, H. (2012) · Advanced Materials · doi:10.1002/adma.201201579 · Cited by 106 · see citing works
Yoon, S., Varghese, S., Park, S. K., Wannemacher, R., Gierschner, J., & Park, S. Y. (2013) · Advanced Optical Materials · doi:10.1002/adom.201200064 · Cited by 99 · see citing works
Li, Y., Shen, F., Wang, H., He, F., Xie, Z., Zhang, H., Wang, Z., Liu, L., Li, F., Hanif, M., et al. (2008) · Chemistry of Materials · doi:10.1021/cm801427s · Cited by 92 · see citing works
Amplified spontaneous emission and lasing properties of bisfluorene-cored dendrimers
Ribierre, J., Tsiminis, G., Richardson, S., Turnbull, G. A., Samuel, I. D. W., Barcena, H. S., & Burn, P. L. (2007) · Applied Physics Letters · doi:10.1063/1.2761833 · Cited by 88 · see citing works
Kim, H., Schulte, N., Zhou, G., Müllen, K., & Laquai, F. (2010) · Advanced Materials · doi:10.1002/adma.201003797 · Cited by 83 · see citing works
He, F., Xu, H., Yang, B., Duan, Y., Tian, L. L., Huang, K., Ma, Y., Liu, S. Y., Feng, S., & Shen, J. (2005) · Advanced Materials · doi:10.1002/adma.200501239 · Cited by 72 · see citing works
Varghese, S., Yoon, S., Calzado, E. M., Casado, S., Boj, P. G., Díaz‐García, M. A., Resel, R., Fischer, R. C., Milián‐Medina, B., Wannemacher, R., et al. (2012) · Advanced Materials · doi:10.1002/adma.201202525 · Cited by 68 · see citing works
Controlling the Structures and Photonic Properties of Organic Nanomaterials by Molecular Design
Yao, W. F., Yan, Y., Lin, X., Zhang, C., Li, G., Zheng, Q., Zhao, Y. S., Jiang, H., & Yao, J. (2013) · Angewandte Chemie · doi:10.1002/ange.201302894 · Cited by 60 · see citing works
Two-photon excited highly polarized and directional upconversion emission from slab organic crystals
Fang, H., Chen, Q., Yang, J., Xia, H., Ma, Y., Wang, H., & Sun, H. (2010) · Optics Letters · doi:10.1364/ol.35.000441 · Cited by 58 · see citing works
Lasing from Epitaxially Oriented Needle Crystals of a Thiophene/Phenylene Co‐Oligomer
Mizuno, H., Ohnishi, I., Yanagi, H., Sasaki, F., & Hotta, S. (2012) · Advanced Materials · doi:10.1002/adma.201104182 · Cited by 55 · see citing works
Rao, G. V. R., & López, G. P. (2000) · Advanced Materials · doi:10.1002/1521-4095(200011)12:22 · Cited by 54 · see citing works
Packing Modes of Distyrylbenzene Derivatives
Bartholomew, G. P., Bazan, G. C., Bu, X., & Lachicotte, R. J. (2000) · Chemistry of Materials · doi:10.1021/cm991194o · Cited by 52 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Organic molecular aggregates: From aggregation structure to emission property
Ma, S., Du, S., Pan, G., Dai, S., Xu, B., & Tian, W. (2021) · Aggregate · doi:10.1002/agt2.96 · Cited by 387 · see citing works
Self-citationLuminescence in Crystalline Organic Materials: From Molecules to Molecular Solids
Gierschner, J., Shi, J., Milián‐Medina, B., Roca‐Sanjuán, D., Varghese, S., & Park, S. Y. (2021) · Advanced Optical Materials · doi:10.1002/adom.202002251 · Cited by 304 · see citing works
Liu, Y., Zeng, Q., Zou, B., Liu, Y., Xu, B., & Tian, W. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201810149 · Cited by 249 · see citing works
Self-citationNull Exciton Splitting in Chromophoric Greek Cross (+) Aggregate
Sebastian, E., Philip, A. M., Benny, A., & Hariharan, M. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201810209 · Cited by 125 · see citing works
Zhang, N., Wang, X., Xiong, Z., Huang, L., Jin, Y., Wang, A., Yuan, P.-X., He, Y., & Feng, J. (2021) · Analytical Chemistry · doi:10.1021/acs.analchem.1c04608 · Cited by 72 · see citing works
Distinct Crystalline Aromatic Structural Motifs: Identification, Classification, and Implications
Ramakrishnan, R., Niyas, M. A., Lijina, M. P., & Hariharan, M. (2019) · Accounts of Chemical Research · doi:10.1021/acs.accounts.9b00320 · Cited by 67 · see citing works
Polymorphism-Dependent Enhanced Emission in Molecular Aggregates: J-Aggregate versus X-Aggregate
Ma, S., Liu, Y., Zhang, J., Xu, B., & Tian, W. (2020) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.0c02917 · Cited by 67 · see citing works
Self-citationKeeping the chromophores crossed: evidence for null exciton splitting
Lijina, M. P., Benny, A., Sebastian, E., & Hariharan, M. (2023) · Chemical Society Reviews · doi:10.1039/d3cs00176h · Cited by 61 · see citing works
Park, S., Kwon, J. E., Park, S., Kwon, O., Kim, J. K., Yoon, S., Chung, J. W., Whang, D. R., Park, S. K., Lee, D., et al. (2017) · Advanced Optical Materials · doi:10.1002/adom.201700353 · Cited by 47 · see citing works
Piwoński, H., Nozue, S., & Habuchi, S. (2022) · ACS Nanoscience Au · doi:10.1021/acsnanoscienceau.1c00038 · Cited by 39 · see citing works
Direct Observation of the Symmetrical and Asymmetrical Protonation States in Molecular Crystals
Ma, S., Zhang, J., Liu, Y., Qian, J., Xu, B., & Tian, W. (2017) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.7b01454 · Cited by 38 · see citing works
Self-citationAggregation structures of organic conjugated molecules on their optoelectronic properties
Zhou, J., Zhang, W., Liu, L., Xie, Z., & Ma, Y. (2016) · Chinese Chemical Letters · doi:10.1016/j.cclet.2016.05.014 · Cited by 36 · see citing works
Liu, Y., Zeng, Q., Zou, B., Liu, Y., Xu, B., & Tian, W. (2018) · Angewandte Chemie · doi:10.1002/ange.201810149 · Cited by 33 · see citing works
Self-citationTang, B., Zhang, Z., Liu, H., & Zhang, H. (2017) · Chinese Chemical Letters · doi:10.1016/j.cclet.2017.08.045 · Cited by 27 · see citing works
Dai, S., Li, X.-Z., Liu, J., Zhang, C., Hu, J., Liu, Z., Fang, H., Sun, H., Xu, B., & Tian, W. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202414960 · Cited by 20 · see citing works
Self-citationBoosting Stimulated Emission via a Hydrogen‐Bonded Co‐Crystallization Approach in Molecular Crystals
Ren, H., Hu, J., Liu, Y., Liu, Y., Xu, B., & Tian, W. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202411911 · Cited by 19 · see citing works
Self-citationNull Exciton Splitting in Chromophoric Greek Cross (+) Aggregate
Sebastian, E., Philip, A. M., Benny, A., & Hariharan, M. (2018) · Angewandte Chemie · doi:10.1002/ange.201810209 · Cited by 16 · see citing works
Ma, L., Liu, Y., Zhao, Y., Sun, X., Zhang, Y., Yin, A., Cao, D., Chen, Q., & Gao, G. (2023) · Applied Surface Science · doi:10.1016/j.apsusc.2023.156422 · Cited by 13 · see citing works
Pick and Place Distributed Feedback Lasers Using Organic Single Crystals
Ma, S., Wei, M., Rajendran, S. K., Karl, M., Xu, B., Gather, M. C., Tian, W., Turnbull, G. A., & Samuel, I. D. W. (2020) · Advanced Optical Materials · doi:10.1002/adom.201901785 · Cited by 13 · see citing works
Self-citationHe, X., Zhao, J. F., Tan, Z., Zhao, J., Cheng, X. L., & Zhou, C. (2020) · CrystEngComm · doi:10.1039/d0ce00404a · Cited by 12 · see citing works
Bhuin, S., Chakraborty, P., Yogeeswari, P., & Chakravarty, M. (2025) · ACS Applied Bio Materials · doi:10.1021/acsabm.4c01817 · Cited by 10 · see citing works
1,3‐Diaryl‐β‐diketone Organic Crystals with Red Amplified Spontaneous Emission
Tang, B., Zhang, H., Cheng, X. L., Ye, K., & Zhang, H. (2016) · ChemPlusChem · doi:10.1002/cplu.201600451 · Cited by 10 · see citing works
Nayak, N., & Gopidas, K. R. (2019) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.9b05430 · Cited by 10 · see citing works
Li, W., & Xie, Z. (2024) · Chemistry - A European Journal · doi:10.1002/chem.202403908 · Cited by 9 · see citing works
Dai, S., Li, X.-Z., Liu, J., Zhang, C., Hu, J., Liu, Z., Fang, H., Sun, H., Xu, B., & Tian, W. (2024) · Angewandte Chemie · doi:10.1002/ange.202414960 · Cited by 4 · see citing works
Self-citationThe light detection performance of Al/VNPB/n-Si Schottky photodetectors for a wide-range spectrum
Yıldız, D. E., Manfo, T. A., Hussaini, A. A., Yıldırım, M., & Gündüz, B. (2026) · Optical Materials · doi:10.1016/j.optmat.2026.118130 · Cited by 3 · see citing works
Funabiki, K., Yamada, K., Matsueda, H., Arisawa, Y., Agou, T., Kubota, Y., Inuzuka, T., & Wasada, H. (2021) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202001638 · Cited by 2 · see citing works
Enhanced Hydrogen Peroxide Photosynthesis Using X‐Packed Cocrystal Catalysts
Wang, L., Deng, J., Li, S., Liu, H., Liu, K., Lv, X., Zhang, Y. Z., Li, J., Bai, S., Zhu, Y., et al. (2026) · Advanced Materials · doi:10.1002/adma.73295 · Cited by 1 · see citing works
Boosting Stimulated Emission via a Hydrogen‐Bonded Co‐Crystallization Approach in Molecular Crystals
Ren, H., Hu, J., Liu, Y., Liu, Y., Xu, B., & Tian, W. (2024) · Angewandte Chemie · doi:10.1002/ange.202411911
Self-citationSun, H., & Hu, Z. (2025) · doi:10.1002/9781119694144.ch10
- Authors
- Ma, S., Zhang, J., Qian, J., Chen, J., Xu, B., & Tian, W.
- Affiliations
- Jilin University (CN)
- Corresponding author
- Xu, Bin
- Tian, Wenjing
- Venue
- Advanced Optical Materials
- Publisher
- Wiley
- Published
- 2015-02
- Volume
- 3
- Issue
- 6
- Pages
- 763-768
- ISSN
- 2195-1071 (ISSN-L)
- OpenAlex
- W2006743672
- Cited by
- 30
- References
- 36
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 5 · 2023: 2 · 2022: 1 · 2021: 4 · 2020: 3 · 2019: 2 · 2018: 4 · 2017: 3 · 2016: 2
- FWCI
- 1.22
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Advanced Optical Materials (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Electrical and Electronic Engineering › Organic Light-Emitting Diodes Research
- Physical Sciences › Materials Science › Electronic, Optical and Magnetic Materials › Nonlinear Optical Materials Research
- Keywords
- organic single crystals, spontaneous emission, stimulated emission, amplified spontaneous emission, organic light-emitting materials
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
